-small job $1300. Gutters, downspout repair, siding etc
-good reviews on angis list, has his company registered as a LLC, referred to me by a local contact 
-can provide proof of insurance but will not add me to it ...

Property Could be Added on to Make it A Triplex.

If I were to get my park back up and running, I would be adding the ability for the trucks to plug in (cut down on generator noise and exhaust - I would charge for access or build it into the rental fee, and most food truck operators would love this option), add real bathrooms, and add other features as an additional draw to get customers for the trucks. 

If someone were onboarding with a new property management (PM), is it customary for the PM to be asked to be added additional insured to a homeowners insurance policy? 

Loopholes can be a great tool if used correctly.One thing I would suggest is reach out to a few agents here on the BP forum in the states your searching and ask to be added to their 'Hot Sheet".

It is a very simple calculation and yes depreciation would be added back as it is a paper loss. 

I would get ahold of @Austin Davis  I would also like to be added to this if possible!

Will plumbing, gas lines need to be added/moved to make this kitchen?

If you dig further into the IBC (and associated Massachusetts amendments per 780 CMR), then you will find the requirements for a sprinkler system to be added for such a conversion or new construction in a three family.

I might be adding a non-refundable deposit on top of that too. ($200?)