Investment Info:Large multi-family (5+ units) buy & hold investment in Tuppers Plains.

Feel free to reach out if you have any questions.The Short- Term Rental Loophole ExplainedThe Short- Term Rental Loophole Explained

I purchased this before deciding to get in to real estate.I am trying to decide if I should rent the property out or sale it to buy something with long term investment in mind.

Setting up direct bookings is a great way to save on fees, but you’re right—it requires extra effort to ensure everything runs smoothly.For vetting guests, start by asking a few questions when they inquire, like the purpose of their stay, how many people will be there, and if they’ve stayed in short-term rentals before.

If you had $50K in a Self direct IRA how would you leverage that to yield short and long term dividends? 

Mistakes I see people make is they plan on living there a short time and over renovate the property where they will never get the money they put into it back. 

you'll probably still need something long term like software as others have suggested but this was a thought i had... you could see the actual profit or loss from a tax perspective for each property.

My idea to achieve this is to convert the studio into a short-term rental.I’m trying to determine if I’m forcing this deal to work by relying on the short-term rental strategy or if it’s a reasonable approach given the numbers.

You’d need a clear exit plan and enforceable lease terms to protect your investment.Think about the following:Tenant Risk – Can they truly recover financially, or will you face another eviction situation?

And if so, to what % of "ok, this could happen" did you hold?