All Forum Posts by: Daniel Murphy

I have a STR down there & drove down the day after Ian to clean up the property. I freaked out a bit as neighbors told me that it would take years for the area to get back to normal & trying to get me to shift my house to LTR (so their friend could rent it). After coming back & getting more bookings for contractors, insurance adjusters etc, we decided to keep it a STR.
We're not worried about the long term health of the area.  

Thanks @Jesse Goswick, that helps to clarify.  That means that you'd be doing a qualified to non-qualified transfer.  

In this case, you've never been taxed on the qualified plan contributions. There will be no cost basis, the entire account will be taxable at ordinary income to you plus a 10% penalty if you are younger than 59.5 years old.  

No matter how you move the money, you'll be taxed & penalized (depending on your age). Normally, I would not advise this however every situation is unique. For reference, we cashed out my wife's small IRA's earlier this year (<$10k) to help fund our first STR purchase. So while there are "generally not advisable" rules, that doesn't mean it wouldn't make sense.

If you were a client or prospect of mine, I would want to first talk through your overall financial situation to see if there are any other options. Or at least I'd want to run the numbers for you so you can go into this decision knowing all of your options & financial costs. 

A few things to talk through. In my head, when I hear someone "got $100k" or another large chunk, I assume it to be in a non qualified account. IE, not a 401k or IRA. Meaning it has different tax rules.

If your dad is retired and your mom is still working, it's possible that they are in a fairly low tax bracket. When I have clients in a low tax bracket and a decent chunk of money available outside of a 401k or IRA, I talk them through potential partial roth conversions.

The theory is that any money your parents saved into their 401k's while working was probably done pre-tax & saved them potentially around 22% in taxes (most common joint tax rate). If they are retired & now in the 12% bracket, they could convert funds from their IRA/401k over to a Roth. Use the $100k in taxable money to help pay the taxes & anything they need to live. Doing this locks in the 10% tax arbitrage gain (they saved 22% initially & paid 12% upon conversion).

This is obviously frought with assumptions... I echo with everyone else here though, there is a lot of info missing to make an accurate recommendation.  I'm just throwing out another idea that is not commonly discussed. 

There are a few things in your post to clarify first but... 

"Annuity from an old job" typically means a pre-tax 401k. More likely a 403b from a school, or hospital if it's in an annuity. What type of employer was this from?  IE- this is likely a "qualified" account. 

Most people's definition of a brokerage account is a taxable investment account.  IE- non qualified. 

You "can" roll your old qualified account to a non-qualified account, but you will be taxed on the entire amount at ordinary income rates. Plus 10% if you're younger than 59.5.  

Most common situation is you would roll your old 401k/403b "qualified" plan into a "qualified" traditional IRA. This would avoid taxes. You could potentially withdraw $10k for a first time home purchase and avoid the 10% penalty.

Look at the account statement from your old plan. If it says "Jesse Goswick, (401k, 403b, 457 etc.)", it's a qualified plan. 

Look at the account statement from your brokerage account. If it says "Jesse Goswick, tod, jnt or jtwros", it's a non qualified plan. 

There's a lot more to this, hard to put all in a response. Reach out to me if you have questions. I'm always willing to help out a CC resident :) 

I've used a CPA in the past, but I've learned that I can handle most of my personal returns by myself.  With the IRS adding tons of money to audit enforcement, will a self employed tax return with various real estate schedules raise any audit red flags if I filed my taxes on my own, vs if I have a PTIN? 

For context, I'm a financial planner by profession & have gone pretty deep into tax planning. I only have one short term rental property but I plan to do a cost segregation study this year.  

I'll get a professional cost segregation study done. I've tracked all of my expenses & material participation hours religiously... What are your thoughts on doing your own taxes in a situation like this? 

I've been to FinCon before & have planned to go since but can't make it this year. It's more geared towards financial content creators. If you're in that space at all, it's THE event.  There are a lot of people in the real estate subgroup also so it would be a good place to connect with other RE investors. 

thanks @Leslie Anne Morris, I appreciate the advice.  I'll add one more wrinkle to this & would love your opinion. 

We're also building a local area guide. www.capecoralforfamilies.com  

The purpose of this is to eventually rank in Google for people searching for activities in the area.  If we can get this to rank well (which I believe based on past experience we can), this alone should bring people to our direct booking site.  

@Dave Stokley, I partially agree & see your point. This will likely never replace airbnb & vrbo. But, the point is to build an extra leg of security. Plus, if any marketing efforts bring 1 extra booking per year, that can be hundreds if not thousands of dollars for us. I'm not looking to go crazy, but like most other things. Once you setup the initial framework of something, the maintenance is usually pretty easy. And with time, it should only help our listing... 

Hey all, I'd really like to work on a comprehensive marketing plan for our STR. I think we've done about as much as we can to rank well in the Airbnb & VRBO sites specifically. I'm thinking of total overall marketing.

Like having the name of our place be something that's easily searchable in google. an @tag in our listing to show how to find us on social media, linking in our direct booking site etc.  

Does anyone have good examples, blog posts or people I should talk to about how to best put all of these puzzle pieces together?  

Thanks in advance. 

For context, we built a local area guide (under construction) for our STR area. This also includes our direct booking page and every page of the website, has a link to our direct booking page. With time, we hope to build more articles & get this to rank in google which should bring more direct bookings.

1) If a guest asked for recommendations (through the Airbnb app) for local attractions, restaurants etc.   Currently, we have not sent the link to our website because it contains a direct booking link. 

2) We also send out a handful of links to private youtube videos we put together for various FAQ's (how to use door lock, pool cover, unlock interior doors etc.)  I'd like to add an outro to these videos with a link to our local area guide / direct booking site 

My question is, how closely does Airbnb monitor these links through their messaging app? IE - we don't want to get red flagged or kicked off of the platform because we are promoting our own direct bookings.  However, if it's a link at the END of a youtube FAQ video, will Airbnb ever see it?  
What are your thoughts on all of this? I want to tread carefully & stay below the radar... 

We'll see if this is helpful or not. Here's our breakdown.  

We pay for Owner Rez ($35) to manage between VRBO, Airbnb & our direct booking site. It also automatically sends out our legal agreement. 

Pricelabs ($35) for our pricing data.  Not a ton of monthly costs.  

When a guest books, I send a quick reply message. I do cut & paste the link to the legal agreement from owner rez in this message so it's not 100% automated.  This takes about 2 minutes even if I'm on my phone to go to owner rez, copy the link & then to Airbnb to paste it into the quick reply.  

I add the guest info to my cleaning calendar, 1 minute. We can integrate this into owner rez to happen automatically but I just haven't done this yet. 

Then I enter the guests door code into my Schlage app, about another 2 minutes. 

While the guest are staying in our home, they may have some questions. This is guest-dependent but most guests are pretty easy. For an average guest stay, I have maybe 5-10 minutes messaging back and forth. 

Our cleaner shows up & clean the property, we do not need to spend time arranging this. Occasionally we have to deal with an issue or a maintenance item.  On average, this is maybe 15-30 minutes per month.  

Once the guest leaves we review them, 2 minutes. 

All this is to say that self managing is not hard, costly or labor intensive. 

More importantly, you need to make the decision that's right for you. It's good to ask these questions to get different perspectives so that you can feel comfortable with your decision.  

For me, I love hospitality. I love guest feedback. I love ownership (of my home & my outcome). Real Estate, finances, interpersonal skills & handy maintenance skills are all in my wheelhouse so it's not hard for me.  Plus, I want the material participation for Cost Seg reasons... 

I can't imagine any reason why I would pay someone else ~ $1k per month to do all of this for me. 

Hopefully this helps a bit for perspective...