I am specifically looking in Essex county, MA because I want to house back close enough to my current W-2 job.

It's an STR, hotel and house hack all in one 😊

If you want to sell this property, you need to let someone inspect it at least once and the discount for due diligence needs to be worth it. 

I have some in-house laborers for any large projects but sometimes value add can even be raising rents to market or finding an off market gem. 

LTR and MID term are hot now as well, we have more people that want houses than houses to rent to them.  

I am looking at different loan options but to break even (not having to put any money of my own in the house after the initial down payment) the current down payment required is that much. 

You are only adding complications and costs with the LLC with no upside  This is all assuming there’s been almost zero appreciation and you shouldn’t sell tax free while you have the chance. 

The investor if they slip and the lender if they need to take the house back.  

I told her no and then she told me to sell my crypto, sell my stocks, apply for credit cards and offered me financing.

It's NOT a house!