House hacking vs Remote Investing

[Eugene Lubman]

Hi everyone,

I am a newbie investor living in the South Shore area of Massachusetts. My original plan was to buy a four-unit property and rent out three of the four units. I will need to occupy the largest of the units since I need a 3-4 bedroom unit for my family. The best deal that I have been able to find in my local market will only start to cash flow (just barely) after I move out a couple of years from now, but certainly not before: the monthly net income based on the 50% rule is $2050 and the mortgage P+I plus PMI is $3000-32000/mo (depending on the loan). Besides, this will require me to give up the house we are currently renting (which we love) and move to a less desirable town further away from Boston. Is this the best that I can hope for in this market?

The alternative that I am considering is to stay put in our rented house while investing in a multiunit property in a market with a better cash-flow potential (lower price-to-rent ratio).  The closest such market that I have found is the New York Capital District: Albany/Troy/Schenectady.  I have found some properties that should (theoretically) give me a healthy cash flow of $2000/mo or so, again, using the 50% rule.  Is this a better option in my case, or this too risky/complicated for a newbie?  Can I even get a commercial loan in the current climate?

(BTW, I am planning to buy and hold, and I am primarily focusing on cash flow, not on appreciation at this stage.)

Any advice is highly appreciated.