It often takes months to get your properties posted, and getting in touch with the Tampa Housing Authority is embarrassingly difficult.

Last year, the city required a bank statement, which was not overly difficult for me to produce; however, this year the city of Chicago required either a homeowners exemption or a state license showing the exact address and unit for the listed AirBnB. 

If you’re looking to scale, then it can be very difficult.

Exterior work is difficult from Mid November through late March, but most of it can be done besides painting.

No, as I mentioned I have LTR rentals but it's becoming difficult to keep buying these when I don't get any immediate tax benefits from them, I've bought two in the last 2 years and had to put out a bunch of money to get them ready, etc and not one cent of that is a writeoff for me until years in the future when I actually have passive profit, meanwhile I live in a high tax, high COL state.

Quote from @Brady Ascheman: Hi everyone,I have recently found it very difficult to find any long-term rentals that will cashflow.

It's the worst because it's pretty difficult to navigate if you don't have someone experienced to guide the way.

I have been trying to sell it to build more, but that has been difficult due to the high interest rates freezing the market...

out of state BRRRR is incredibly difficult. 

However, if you are looking to grow your money or make income from raw land it is very difficult to do so.