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. 

The current incentive structure makes it very difficult for an assumable mortgage to actually be a tangible tool for buyers. 

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.

@Delmar Marsh JrAs you begin your investing career I would suggest using this website to get a general idea of the area you are looking to invest in. https://www.areavibes.com/Its a great starting point and gives you a whole list of data that you can look through. 

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.

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

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.

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