When going incognito on booking platforms, our place is really difficult to find.

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

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

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

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

Out of state seems harder to break into simply because I'm not there - maybe Hoboken /Jersey city or further like @Eric Hajdu mentioned are better places to start.Out of state is not difficult to get into. 

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

out of state BRRRR is incredibly difficult. 

and it's also difficult to find 80% LTV these days.  70-75 is more likely.