Hello, I am interested in my finding my first multi-family deal upon the last year and half of research, I have recently kicked it into second gear and on course to obtain my first MF. I work full time, my company has an office in Middletown and Boston, my thoughts would be to owner occupy finance a home and house hack in either of those markets however most of my market research has been in the Middletown, Connecticut for its more affordable price point. As my work enables me to travel often, setting up a home residence would be a great way to begin investing especially since I could get friends to fill my portion of the residence with me.

Boston is quite expensive and positive cash flow seems unattainable unless I decide to add a lengthy commute into my life which seems to be a non option at this point. I have also looked into Glastonbury and West Hartford CT markets however the price points in these markets is already much too high to earn positive cash flow. 

Middletown, CT does not seem to be poised for too much growth with high unemployment figures and slower than national average job growth. However, I like certain aspects of Middletown, including its hipster downtown area, Wesleyan University, Middlesex Hospital and proximity to the river. I am worried I should not invest in a town (or potentially state for that matter) that appears as it is not on the path of growth. I do believe I would be able to ascertain positive cash flow (duplexes and triplexes for 125k-250k with reasonable rental rates $1200 or so per unit for 3BR/1BA) which keeps me interested. From the several properties I've dug into, my results yield positive cash flow. I am concerned with the state as a whole for several factors, high property tax (3.33%), bleak outlook, i am curious to know if this is worth jumping ship and time to look elsewhere or shall i keep digging?

Upon numerous mixed opinions I know certain people that swear away from it and some as Connecticut in general, and others who see its potential. The property prices have been somewhat stagnant I believe, even during the downtown. My question going forward is, is it worth investing in Middletown? How does Connecticut look as a whole. Is it worth looking at other markets in the country? Are my expectations and assumptions accurate? As a long term strategy, am I barking up the wrong tree? Would buying my first residence with owner occupied financing in Middletown, then move to another market for my next MF a reasonable strategy. Im at a bit of a cross roads, any incites would be much appreciated! Thanks in advance. Chris.