While I would never invest in NY as James mentions as its the worst - if I was going to do it I would atleast make sure I tried to follow the rules. 

Literally might be the worst advice on these forums right above.

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.PM us if you’d like to discuss this logical approach in greater detail!

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.

I am going to rework it and have it as 'worst case'.

I am hoping to find distressed properties that I can buy with all cash for BRRRR and am also open to any sort of partnership.

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

.- 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?

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).

Bottom line....nothing is "grandfathered in" usually, inspectors don't care about holding costs and there are very few cosmetic only rehabs that don't require some sort of inspection.