Other than that, mistakes related to expenses are common, and not electing things like the De Minimis Safe Harbor election, which can save you if you get audited.An option you might want to consider if you do your own taxes is at least have a tax professional review your return after you complete it (but ideally before you file it). 

I have a 23 unit condo building in Chicago, and I currently own 22 out of the 23 units with the intention of buying out the last unit. I have heard from some people, but have not gotten a definitive answer, that going...

Hi @Steven De Lange,   Thanks, yes, it works fine with a full-service property manager - would be nice to be able to find that rent collection service a-la-carte...

I own a single-property home in Delaware.

Prices skyrocketed from massive government actions and those actions first stimulated demand and later de-stimulated supply.People are not buying because they have more knowledge now...it's actually the opposite, transactions are at record lows.

Quote from @Steven De Lange: BRRR out-of-State is a great strategy if you have a good team of people in the area you are looking to invest (realtor, property manager, and contractor/ project manager)- a team you can build through BP. 

Would any investors (especially those in short-term rentals in Wilmington, DE and Pittsburgh, PA) be willing to chat?

In Delaware a 5 day grace period is mandatory so you can't collect a late fee until the 6th. 

Quote from @Paul De Luca: Quote from @In Cho: Hi,I'm a veteran looking to get started with house hacking in the Chicago area, and I'm hoping to get some advice from more experienced investors.

They seemed to think PMs were Cruella de Ville.