Being scatter brained will make things difficult to get done.

@Sathya Priya Sampathkumar you will find it difficult to find something in the Cambridge area.

if you pick a random property in Akron (i was just there, randomly) that you haven't seen, that's listed on Zillow, and turn it over to people you haven't met to manage, it is nearly guaranteed that you will lose money.if you're serious about this, i would recommend that you go there in person, meet agents in person, build a network in person, and conduct your property search in person.and if you can't go there in person - i wouldn't give up on Oregon. i know, i know, you're going to tell me it's 'too expensive.' and so yes, it's difficult. 

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.

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

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.