Your friend will have a difficult time with rentals because he's not screening the applicants or enforcing the lease well enough. 

Both of those towns have stringent rules about STR's that can make it more difficult to find the right property that will fit your strategy.

That was one of the most difficult and time consuming things when I was managing my own properties.

it is very difficult - much more difficult than advertised, and more difficult now than it was a few years ago because of the increase in interest rates and the heightened competition for distressed deals.the issue is this: you're up against other investors and businesses spending tens and sometimes even hundreds of thousands of dollars a month on marketing. 

 @Greg Abel I think it's important to consider the long-term, as changing property management software is difficult.

With the new NAR ruling it's making things even more difficult.  

Hi Haoyang,It's pretty difficult to find, but just with the resources available to me I was able to spot a few fourplex listings that were somewhere around $1.25M.

It is so difficult to police and enforce guests, I would focus on the increased water bill. 

Detroit would be a difficult market to utilize a DSCR loan in due to the low amount of monthly rental income coming in. 

It is difficult doing this from a distance.