welcome @Cam Caraher and congrats on joining BP, this place is the start for many, sure was for me longer ago than I care to admit.I'm not personally in your market, although was born in dorchester and grew up in NH, but this is a great place to meet locals.If you have not already a great starting point is the Meetups posted here, just search for your area and see if any meetups are happening. 

I signed a voucher for a home on November 7th and it was turned in on November 8th.

What type of renovations are best on a house hack if the goal is to BRRRR every year?

I thought I would bump this topic back to the top based on the fed cutting the federal funds rates a .250%.  

And 0% deduction on expenses related to the live in unit.

I think it depends on the problem.

Not sure if you were looking for a long-term hold on a two family, but it seems that was not playing out favorably for you. 

But how much do you spend annually on all these, just curious?

Quote from @John Kelly:I would agree with @Ashish Acharya, #1 is the best answer to the question on his response in the reason it would not be good to use an LLC on a house hack until you move out of the house and call it a true rental. 

Also very passionate on multifamily.