the safest way is to just work like a maniac basically do your regular job and do REI as well, you will be putting in 50-70 hours a week but its safer than gambling that your REI will take off right away.

Its a gambling contract.

To me it seems like a gamble.

Church Hill is one of the top up and coming neighborhoods but the deals are in the rough sections, which may get gentrified but it's a long wait and sort of a gamble in my opinion.I'm looking for a SFR now to live in and rehab, preferably in any decent area.

Do most bigger groups/portfolios use off-shore insurers for this?

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." 

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

You will also be taxed by US 15% by the US given the taxation treaty on any dividend distribution, and 12% on any interest you pay yourself from lending the initial funds to the company.It seems to me that a tax specialist you consult with should tell you about these 2 options, and explain to you whether you should loan the initial capital to the LLC, as it seems to me that it could alleviate the concern of double taxation of (1) profit and (2) dividend.You can PM me so we can share what material we have on offshore taxation.

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. 

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.