All Forum Posts by: William Sing

Hey Chris,

Congrats on wrapping up renovations and diving into rentals on Cape Cod! Mixing MTRs and STRs can be a great strategy, but it does take some juggling.

Switching to STRs in the summer is totally doable—you just need to plan ahead. Setting MTR leases to end in May or early June gives you time to prep for the summer season. Be upfront with tenants about lease terms to avoid surprises, and those summer STR rates? Totally worth it to cover any gaps.

For managing it all, a Property Management System (PMS) could save you a ton of time by syncing calendars, automating messaging, and handling bookings. Just keep in mind that STR and MTR-focused systems are often very different, so finding one that does both well can be tricky. If you're exploring options, look for a system with an API that connects to tools like Zapier or Make.com. That'll give you flexibility to automate and integrate workflows as your needs evolve.

A direct booking site is a nice-to-have down the line if you want to save on platform fees and build a brand, but starting with platforms like Furnished Finder or VRBO is a solid way to keep things simple while you’re getting started.

Good luck—sounds like you’re on the right track!

Cheers,
Will

Hey @Zachary Engen,

Congrats on owning the property free and clear! It sounds like you've got a solid plan in mind with the HELOC for your upcoming flip.

I've got a resource that might be helpful as you dive into this—it's a guide covering key questions to ask and strategies for navigating home equity borrowing. It'll help you use your HELOC confidently and align it with your financial goals. You can check it out here: HELOC Borrowing Guide.

For faster pre-approvals, I’d recommend looking into credit unions; they tend to move a bit quicker with these. Here are a few options I reached out to in the past that might be worth a call:

• OnPoint
• Advantis
• Consolidated Community CU
• Rivermark
• Columbia Credit Union
• Trailhead Credit Union
• First Tech
• Umpqua Bank
• NW Community Credit Union
• Key Bank

Key Bank often offers solid terms, but their underwriting process can take a bit longer, so just a heads-up there. Otherwise, credit unions generally seem to prioritize quicker approvals, which could be beneficial for your timeline.

Best of luck with the flip—sounds like an exciting project! Let me know if you have any other questions on it.

Cheers,
Will

Without knowing the condition of the property, that is the main thing. I'd personally be a bit more conservative with the underwriting and make sure to see what the carrying costs could potential get to especially if this is a bigger renovation and not just cosmetic. 

Hey @Devin Voelker,

Glad to see you're jumping into homeownership with a house hack—such a smart strategy! You've already put in some great thought, and with that ADU, you've got a lot of options.

One thing to consider is starting with long-term tenants in the ADU for a bit and then transitioning it to a mid-term rental (MTR) down the line when you feel more comfortable. A long-term rental gives you a steady, predictable income as you ease into being a landlord. Once you've built up some reserves or feel like you're in a good spot, you could switch gears to MTR, especially since you're so close to a hospital.

And later on, you might even mix it up between MTR and short-term rentals (STR), depending on demand. The flexibility of your location near a major hospital opens up a lot of potential to experiment with different rental strategies to see what works best.

One thing to keep in mind, especially right now, is that we’re heading into the "slower" season for rentals. If you aim too high with your pricing and the place isn’t renting out, be ready to adjust quickly to fill the spot. Having a plan to reduce the price or offer incentives can help get tenants in there faster, which is key to keeping your cash flow steady.

Overall, you're in a good spot with that ADU, and with a bit of flexibility in your strategy, you'll have options that can really work for you in both the short and long term. Feel free to reach out if you want to bounce around more ideas!

Best of luck!

Hey Daniel,

Great question! Owner financing can be a fantastic strategy for both buyers and sellers when done right. I’ve worked with investors who have used this approach successfully, so here’s a quick breakdown of what you need to know.

First off, you don’t necessarily need to own the property outright to offer owner financing. One option is to have the buyer use a loan to buy out your existing mortgage, and then you can carry a second lien on the property for the remaining balance. This is often referred to as a "seller carryback" for the second portion. The buyer’s lender will still do underwriting for the full amount of the purchase, but this allows you to finance part of the deal while the lender handles the rest. Just be aware that this adds another layer of complexity, and you’ll want to check with both your lender and a real estate attorney to make sure everything is set up correctly.

When it comes to terms, owner financing gives you a lot of flexibility:

• Interest rate: You want something attractive to the buyer but that compensates you for the risk of holding that second lien.
• Repayment schedule: You can choose a traditional 15- or 30-year schedule, or go with something shorter if you want to be paid off sooner.
• Balloon payment: Many owner-financed deals include a balloon payment, meaning the buyer pays off the remaining balance after a set period (usually 5-10 years). This gives you steady payments but also a quicker exit.

You’ll definitely want to get the contracts and paperwork squared away with a real estate attorney. Typically, you’ll need a promissory note (outlining the loan terms, interest rate, repayment schedule, etc.) and either a deed of trust or mortgage to secure your interest in the property. This protects you in case the buyer defaults.

Lastly, keep in mind that owner financing comes with some risk. You’re effectively acting as the bank, so it’s crucial to vet your buyer thoroughly and possibly require a solid down payment. The second lien also means you’re in a junior position if the buyer defaults, so you’ll want to be aware of that risk too.

Overall, owner financing can be a win-win, but it’s important to have everything structured properly to protect your interests.

Cheers,
William

Hey there, I'm a bit confused on how you are getting the refinance to be at 4% for a cash out refi. If you are buying it using seller carried you might be able to use a HELOC to pull out some of the equity but not sure how the refi.

@John Arena

It sounds like you're experiencing some common challenges with property management that might warrant exploring other options. Evaluating a new property manager (PM) can definitely feel daunting, especially when you're 500 miles away. Based on our experience, here are a few key questions that could help you evaluate a new PM:

1. Revenue Management & Forecasting: How do they set realistic revenue expectations? Ask for their track record with properties similar to yours and how they navigate disruptions (like renovations) while maximizing occupancy and revenue.
2. Communication & Problem Solving: How proactive are they in handling day-to-day issues without needing to involve you? It’s a good idea to get specific about how they plan to address maintenance or operational issues independently, so you’re not getting those 8-10 calls a month.
3. Marketing Strategy: How do they keep your listing competitive on platforms like Airbnb, VRBO, and others? It’s also worth understanding how they adjust pricing to adapt to changing market conditions and seasonality. A good PM should be on top of this and not simply ride out the market shifts.
4. Technology & Reporting: What tools do they use to monitor guest interactions, maintenance, and property performance? Ideally, they should offer you a dashboard or portal where you can easily track performance and minimize the need for back-and-forth communication.

In your case, where revenue has dropped despite heavy investment, the marketing and revenue management piece feels particularly critical. A new pool and "instagramable" design updates should increase demand and pricing, but it’s all about how that’s being communicated to potential guests. The new PM should be focused on leveraging these improvements to your advantage.

Hope this helps! And remember, sometimes a new set of eyes can make all the difference.

Hi @Emily Gowen,

It sounds like you've really put a lot of thought into this, and you're weighing all the right factors. Given everything you've shared, one key thing to consider is flexibility. Selling now could free up your equity, giving you the option to diversify into other investments or markets that align better with your new life on the East Coast. It also offers a chance to shift into something more passive, reducing the hands-on management that seems to be more of a hassle now that you’ve moved.

That said, the rental income potential from your properties is worth noting, but there’s a limit to how much you can boost your cash flow, especially after already making significant upgrades. And, depending on where your properties are in Portland, the value might be near its peak—selling while they’re in top condition could be a smart move.

Ultimately, it comes down to what will give you the most peace of mind and the most flexibility for the future. Whether you sell and simplify or hold and continue to benefit from appreciation, it’s about aligning with your long-term goals and lifestyle. If you do decide to keep the rentals, let me know if you need any property management company recs!

@Brett Sorrell,

Great points to consider! If you're thinking of turning the shed into its own unit, it would require some serious upgrades—like adding a separate electrical panel, sewer, and water connections. That can quickly add up, especially if you're looking to make it an Airbnb. You’ll definitely want to dig into the zoning and permit requirements for your area to get a clear picture of what's allowed and what the associated costs might be.

Also, don't forget to factor in things like parking and whether you'd need to add a kitchenette to make it a viable short-term rental (STR). These are critical aspects that can influence not only your budget but also the overall feasibility of the project.

However, if you’re looking for a lower-cost value add, turning the shed into a high-quality storage space could be a solid first step. Future tenants would likely appreciate the extra storage, and it could make your duplex more attractive in the long run without the hefty upfront investment that a full conversion would require.

Another idea is to repurpose the shed into a functional office space or a private workout area. With more people working remotely, a dedicated office could be a big draw, and a workout space adds value without requiring extensive renovations. These options would still keep your costs down while offering practical benefits that could attract a larger demographic of renters.

Starting with one of these simpler conversions also gives you the flexibility to explore more ambitious plans down the road once you have a better understanding of the property's potential and your own budget constraints.

Hope this helps clarify the options. Whatever you choose, it’s all about balancing cost, effort, and potential return!

Hey @Nicole Farley,

Congrats on diving into the real estate game! You’re already asking the right questions.

Your current house is a solid asset with that 2.75% rate and strong cash flow potential. Renting it out makes financial sense, especially with a $1500/month rental income. Plus, keeping it as a rental helps you avoid any potential loan fraud issues—something worth considering based on your risk tolerance.

The new house could be great for personal reasons, being closer to your parents, but with a higher rate and payment, the financials aren’t as sweet. I’d suggest checking the condition of the new property first—you might need to put in some work if you plan to live there long-term.

While I’m not a tax professional, and you should definitely consult one, keeping your current home as a rental seems like a solid move. But ultimately, balance what works best for your finances and your life goals.

Good luck with your decision!