With the outlined steps and strategies, you can overcome the fear and stress associated with finding tenants for your house hack.

Overcome any failures and just hope they are overweighted by successes.  

Has anyone here dealt with Andersons Adversers before? 

If you are risk adverse real estate, (especially out of state) is not for you.

If you can overcome either of those problems you might have a bigger business opportunity on your hands!

If you can attracts tenants based on location and amenities, your worst case scenario in lean years would be lower income or break even, but not in risk of expenses overcoming your income and default.  

In regards to keepin your name on a lease, the lender may very well consider that rent payment when calculating your DTI, this may or may not adversely affect you depending on your situation. 

How have you overcome any financing issues as a non US citizen or resident?

I think having a down payment of 20% or more is one barrier I will have to overcome.

He likes the area b/c there are tons of service jobs, plus a number of colleges in the vicinity whose employees would have a hard time purchasing in Fairfield County, so the rental market is a vibrant one.I can't speak to flips in Bridgeport specifically, but as a general rule I figure if you price it right and make sure the monthly payment appeals to most buyers, that's how you overcome the high tax issue.