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All Forum Posts by: Jon Martin

Jon Martin has started 30 posts and replied 931 times.

Good call! After all the hard work you owe it to yourself to see it through. You can always change strategies in the winter, although i think that even winter numbers could surprise you. On top of that you need to build up your review base. 

Also, forgot to mention that it's worth keeping it STR through the remainder of the year so that you qualify for 80% bonus depreciation. If you are self managing and can maintain an average stay of 7 days or less, you could be allowed to offset the losses against w2 income (disclaimer: I am not an accountant or tax professional).

Quote from @Tyler Herlihy:

I also like Greenville, SC. I think it has a great little downtown and river area, but I think the city doesn't allow STR so you'd have to go outside the city. It still may be tough at your price point though.

This is correct but doesn't seem to be enforced. Plus there is a state law being discussed that could overrule local laws on this issue. My STR is slightly outside the city limits but only a 5 minute drive downtown. You can still get in for under $300k but you probably aren't going to hit a home run at that price. Would be a decent base hit to get started and potentially some significant upside with appreciation as the town is attracting a lot of attention.

I had a similar inquiry very shortly after listing for June and July. I was tempted because it would've turned a decent profit and relieved some anxiety but I decided that I need to see for myself how the property performs over the course of 4 seasons before I consider MTR. Especially during peak season. Eventually I may go a hybrid route where I MTR in the winter to early spring and then STR in the summer and fall.

I'd rec not taking the bird in the hand! You already put a lot of work in to make an STR so you should really see how it does in peak season.

Quote from @Ray J.:

@Jon Martin - Congrats! Looks like a great property, and the pictures came out really good! Keep those 5 ⭐s going!


 Thank you Ray!

@Shawna Walker I started with American Modern and they seemed okay until I realized that they would not cover theft under any circumstances iirc. This made me nervous. I upgraded to Proper for an extra ~$40/month and their coverage is much more extensive. Theft (even while unoccupied), pet damage, even a guest flushing the wrong thing down the toilet are all covered. I don't worry about my place being left unlocked anymore. 

A similar thread popped up a few weeks back, and some posters shared some interesting data that the 1 bedrooms have better COC return (IIRC that was the metric used) than 2s and 3 bedrooms. The nice thing with a 1 bedroom is you can be more competitive with both your base price and your cleaning fee. Lots of couples and single travelers end up booking 2 bedroom houses even if they only need one bedroom because they want the amenities that typically come with it. I wouldn't write them off.

Post: The STR loophole

Jon MartinPosted
  • Posts 941
  • Votes 794
Quote from @Greg O'Brien:

@Jon Martin the rules have been around since 1986! The “loophole” is just a specific subset of Regulations for transient rentals, which have been around forever, but of course became more popular recently.

The IRS cannot change the law so it will likely not change until a major tax package gets passed but even then, this isn’t a blip on the radar of tax policy.


 I agree, however AirBnb was not a thing at the time they made that rule. My point was that it would not surprise me if congress went after it with the next tax bill. 

@Connor BathI have an investment property in Greenville near the west village. The town is relatively small so it's pretty easy to be within that driving distance of downtown. I would ask your realtor to bring you listings with basements and/or detached garages because it's tough for an MLS search to reliably pick those search terms up. Most of the west side is 2 and 3 beds with smaller footprints so they aren't great for househacking. The North through East to South quadrants seems to have more broad footprint homes and basements where you can carve the house up for more privacy.

What neighborhood? Might work as an STR or MTR, especially if it's close to the hospitals. My STR is near the West Village and Brandon Mill and does better than your estimates as a 2/1. If you can at least break even and hold I think the appreciation will pay off- the town is booming!

For an LTR I would pass on the rehab and it would probably be fine (serious issues permitting). 

Quote from @Travis Timmons:

Perhaps you and I link up and start a marriage counseling business for aspiring short term rental investors.


 my wife has pointed out, "that place looks nicer than our house!" 

I'm like, "well yeah, it's business! We don't make money off of having nice things here". 

Doesn't seem to resonate.