@Chloe Westwood I'm originally from Helena and have a few friends who are involved in real estate in the area.

Many people who got involved in the STR space are actually offloading these units as they cannot get the proper zoning or licensing. 

They take into account the tenant's income, other housing costs like utility bills and market rent for the area. 

This has been a side thing for us, and our accounting has been old school manual spreadsheets, along with rent collection varying from tenant to tenant (Zelle, PayPal, cash app, etc…) neither of us are great at keeping up with accounting which makes tax time a nightmare.

Also, I don't see why you would take the risk of buying it in your own name and moving it into an LLC later...If it's a matter of the bank only taking your personal financial situation into account if you do it in your own name, I'd personally rather use hard/private money to acquire it, then refi with a bank once the property financials stand on its own.

From that point, some sort of banking engine would need to be involved that was sophisticated enough to handle and understand trivial to highly complicated financial transactions.In any case, it would be fascinating to a small niche of people (myself included) so not too likely to become a commercial success.

You’re probably thinking, I don’t know this person so why should I get involved… just remember that we’d both be in the same boat, we both have to trust and respect one another, but read to the end, and learn more about me.I was born and raised in San Jose, California by my beautiful, wickedly smart and fiercely independent single mother.

That would not go well for you I suspect....This is a tough one because you certainly do not want to get involved and wind up being a target yourself.

The former involves lower monthly payments but requires a lump sum at the end, while the latter has predictable monthly payments but might be higher.

And evaluating the track record is a call that's made first by the taxpayer or their CPA, and ultimately by an IRS auditor (should one get involved). it is very true that the IRS cares about intent with respect to capital gains in real estate -- I've certainly seen cases where the statutory timelines were less important and the identified intent of the investor.with respect to determining whether you qualify as a developer or an investor, it's much more of a "forest" than the "trees"...so holding any given investment for 14 months prior to a flip is certainly no guarantee of receiving long-term capital gains treatment.I hope this helps.