.- Im thinking of not charging security deposit because of all the strict MA laws and just using the last months rent as a sort of security deposit, thoughts?

These little things are the things that make guests feel connected to you.The rest will sort itself out!

If not in the city, and not in the ETJ, then it's a lot easier, provided you can get water (probably need to drill water wells so thats a separate ground water district) and sanitation (some sort of onsite sewage treatment).

Seems managing a "property management" team (without taking on properties owned by others) would keep things consistent and allow for minor tweaks without jumping ship from one "complete" PM to another....sort of handling all aspects "in house" but not solo.

In my state (NY) you have to accept these sorts of requests unless you can find a valid reason not to.

I’m curious to see if anyone has any experience in this sort of subject as if it would be easier to buy a home with a building already on it then ask the township for a permit or if we should continue to look to buy and build. 

DM me with what sort of contractor you're looking for and I'm happy to find out for you. 

If you have one close to you, they usually sell all sorts ofstuff pretty cheaply.

Is there an inspection of some sort or do I need to ask the condo association for maintenance records?

I need a checklist of some sort.