The IRS changed how they treat single-member LLCs (solopreneurs like myself) and I expect there will be more changes like in Illinois coming. 

You cannot even apply for an STR permit on a single family home until after you've owned it for five years (and there is no guarantee you will get the permit).

@Khaled El Dorry This strategy is know as a consolidation exchange, and like what @Adam Bartomeo said a single buyer might be difficult to find.

I like both of your ideas so I would look for the single where an ADU is permitted or one with a dump ADU to renovate (that's best) and balance that against the purchase of a 2-4 unit.

If single you would have standard deduction of $15,000 plus LTCG tax bracket of $48,350 giving you room of $63,350 to fit income and converted amounts in before you pay any tax.

Would it be a bad idea to buy a single family home built in mid 1930's?

I'm also not super optimistic on rents increasing over the next year or two though, especially if we go into a recession.

I went through it anyway bc she had a good footprint online, I liked the designs, and a couple of ppl at another STR group recommended her (not an excuse, I was super busy and thought I was dealing with a professional).

We read what you said and we understand it entirely aside from the false accusations you tried to make in your paragraph.What do you want us to sit here and go back and forth with you on every single detail?

That comment also seemed to imply that you don't report the rental on Schedule E if you have an LLC, but that's not correct, with a single member LLC it still goes on Schedule E."