The first house I bought, I lived there rent free, AND mortgage free, while renting rooms to other people.

I'm also finding that a single large repair can wipe out a whole year of income, making me wonder if cheaper cashflowing properties is the right play. 

Feel free to reach out with any questions.

I understand that Dutchtown is more of a cash flow play currently, but is there any appreciation on the horizon?

This is unfortunately part of the game that we play.

Quote from @Austin McDonald: I'm using Capital One at 4.23% Ally: 4.25% APYMarcus: 4.30% APYM1 Finance: 5.00% APY (must be an M1 Plus member, but I believe they’re still offering free trial.  

Since you’re using your own funds for the renovation, that can work in your favor, but some lenders may still be able to fund 90-100% of the rehab costs if you choose to leverage financing for that as well.A few key things to keep in mind:✅ Loan-to-Value (LTV): Many lenders will go up to 70-75% of the after-repair value (ARV), so your projected resale value plays a big role.✅ Luxury Market Considerations: Some lenders may be more conservative with high-end properties, so having strong comps, a clear exit strategy, and a solid renovation plan will be important.✅ Interest Rates & Terms: Expect slightly higher rates than standard fix-and-flip loans, often in the 9-12% range with 12-18 month terms, depending on your experience and lender.

For example, adding little things like a pack-n-play, high chair, and coloring books can attract more families, or a dedicated workstation can help snag business travelers to fill in during the week. 

You can finance both real estate and business-related expenses under one loan.Best for: Owner-occupied properties (51%+), businesses acquiring both property and operations, or those needing working capital alongside real estate.SBA 504 Loan – The Fixed-Rate Power Play✔ Max Loan Size: Typically $5M, but can go higher with green-energy incentives✔ Down Payment: Typically 10% (15%–20% for special-purpose properties)✔ Eligible Use: ONLY for real estate and equipment—no working capital✔ Term Length: 20 or 25 years (real estate), 10 years (equipment)✔ Interest Rate: Fixed, below-market rates (CDC portion is government-backed)✔ Structure:50% Bank Loan40% SBA/CDC Loan10% Borrower Equity (15%-20% for special-use properties)Best for: Buyers looking for long-term, fixed-rate financing with lower equity requirements, particularly for industrial, warehouse, retail, or medical office spaces.Which One Should You Use?

I have a few options in play right now for my goal of adding another property to my portfolio this year, it seems like the Chicago market is yelling at us to invest into single family homes in B+ areas.