Honestly, I think you're estimated expenses are a bit low.

-While rent would be more expensive month by month, the idea of being able to take my equity out of my home and also being able to reduce annual repair costs, property taxes, etc. does seem appealing to me. 

I ended up making a profit that paid for my wedding and honeymoon!

Boston is expensive just as any other major city so you might have to pivot outside of it. 

House hacking with an FHA loan (3.5% down) could be a smart way to start while minimizing living expenses.

An expensive fix that could've definitely been avoided

Ultimately after 15 yrs the mortgage has been paid down so cannot complain much.

now, if you've boosted the ARV of the house via the rehab to 200K, you can do a cash out refinance, and put a long term mortgage on the property that is paid monthly.you will get "cash out" (minus closing costs) at closing. 

It is very expensive to miss filing dates, so file now.Remember, File ALL of your entities (Corp and LLC).Watch for updates on this.

Ofcourse my mistakes would cost me if done all my self as well.So i am thinking that by going through paid consulting, it saves me from mistakes and time.