Sounds like you've got extremely limited knowledge and skills in this business and are already profiting off of a massively profitable business.

Real estate gets easier when you have money, but starting out is extremely hard. 

Boston is extremely unique because of the limited land, housing stock, and very high prices.  

- If I want to make any improvements / renovations to the property and have to get permits, could those trigger inspections then a tear down? 

Pulled the trigger on my first deal!!

My concern is triggering a "Due-On-Sell" clause and that the life of the loan will be under our personal names and not the LLC. 

She's extremely difficult to work with because she doesn't have a working phone number.

Will this trigger “Due on Sale” ? 

If you have new plumbing, electrical, windows, HVAC, and a new roof you are in good shape.If they Mechanical’s are extremely old you are better off creating line item costs and projecting their replacement date.

I've read the books and done the research to know what markets work for my goals, but mentally I find myself nit picking every market trying to find the "perfect" fit which leaves me to never pulling the trigger. any advice on how to overcome this so I can finally get my real estate dreams underway??