Boston Newbie - the single family versus multi-house-hacking

[Mick Glover]

This is my first post, but I've been scouring the forums learning as much as I can. First thing I have to say is that I think BP is amazing. Listening to the podcast's during my commute each day has been informative and a form of educational stress relief.

I'm originally from Florida, living in Boston (Jamaica Plain area) as a renter for the past 3 years, looking to invest in real estate. 

I've read many of the posts about the difficult/nearly impossible task of house hacking in the central Boston area. I created my own excel model based on one of Brandon's posts and came to the sobering truth that the numbers don't look great when a duplex in JP costs over 600K, but the rents come in around 2k per unit at best. Whereas many people recommend living further out, this isn't feasible for me based on work requirements. 

So, I'm back to thinking about a buy and hold strategy where I live in the condo (or single family if I could find one) and then maybe moving in a year or two.

I ran the numbers today assuming an FHA loan (to minimize my cash outlay) although MassHousing may be a better option that I will look into and this is what I came up with. I would love to get any feedback on my thought process.

RENTING: 
If I rented a $2400 apartment, then I would spend $31,200 (including the one month fee, which is absurd) in one year.

BUYING:

Then I ran the numbers of the cost of "ownership" assuming the following

375k purchase price condo/SFR, 5k in improvement, FHA financing, 5% down, 30 year (including 1.75% upfront MIP and 0.8% annual MIP), interest rate of 3.625 (pre-qualified by TD Bank). 0% appreciation, 1.5% property taxes, homeowners insurance of $35/month/$100K home value, 200/month in HOA fees and $3,000 in annual maintenance. I did not account for any potential tax benefits and I did not include utilities because I "assumed" the costs would be similar wherever I live. However, i did take into account equity accrued.

When I ran these numbers, my "return" for year 1 is NEGATIVE 28,000?

So is it worth doing the buy and hold strategy where I may gain $3000 over the renting (NEGATIVE $31,000) in year one?