Appreciation (over a 3-4 year period) is speculation and no different than gambling.  

Nor does the mortgage company want to gamble on whether or not the borrower will have sufficient funds to pay when do.  

It is gambling in some sense but I really don't see Southie going down anytime and only becoming more desirable as G.E, Reebok, Amazon move to the Seaport and as Andrew Square and South Bay get developed." 

I simply want to find a job that is closer but still pays well.I feel as though house hacking would be the only option I can do right now in time but I also don't know if I enjoy my position enough to gamble that I would be here longer than the next few months.

If you don't know what your buyers criteria is then it's a crap shoot and that's something I don't want to gamble with.

Sometimes its the gamble you have to take.

It's a gamble, and it's rigged to benefit the house.

Not having the right capital and right fix and flip can put you in a really hurt position especially if you're gambling your families money and wind up in a stuck in the middle position. 

Yes our research says that it would be a gamble and not  much cash flow if any at the1500s.

Saving it for equity growth is a gamble.