Absolutley Dave , just walked in door after wading thru the snow on my snoshoes and dreams of palm trees and warm ocean breezes somehow came wafting thru the house.

Not everyone's cup of tea, but worked great for me; 2) Rent it out.

In my opinion the best advice I would give you is from the saying "When is it the best time to plant a tree" the answer is 20 years ago and when in the second best, and the answer is now.

For your first rental, I would stay out of the Tree streets or French Hill, if you are buying in Nashua proper. 

(Because the blind squirrel knows what to look for, the nut, and where to find it, under a tree.)

Other than parts of Boyle heights, I have not looked into these areas very closely since they're not my cup of tea. 

have seen homes on similar size lots go for around 150k. the land is just sitting there for several years going on decades. the shrubs seem to be well on their way into growing into trees; is there like a service that clears lots for a fee, or maybe it would be more cost effective to put a (manufactured?)

Charge him for the dead trees?

I'd like to do it to the other side of the house as well but the neighbors have some oversized trees right where it'd be and probably not a fight I want to have to get them removed/ trimmed properly.

@Tea Houck I fully agree with @Chris M., stay away from HOA's.