I have my contractor walk through it instead of a home inspection.Once you do a few, you learn to expect pipe bursts and leaks, sewer backups, etc so just factor those into your rehab estimate.The big question if you are looking to wholesale is -(a) I believe HUD has a restriction on the deed saying you cannot flip/wholesale it.

You are absolutely correct about the importance of understand which townships allow STR's, and also knowing the HOA restrictions for specific areas as well. 

Myself if I thought with my big trees next to us same thing 100 foot tall 4 feet at breast height I would not ask I would just take care of it and deal with it later.

Are there any regulatory restrictions preventing sponsors from directly selling theirs DST?

I have plenty of clear height (24-28'), acreage, parking, and the right zoning to do this and I am located in a mid-major market.

There are also some restrictions on the property only being one unit, close proximity to your primary residence, among other restrictions. 

You can restrict guests in a room hack, but you have to be reasonable.

Basically a restricted unit can definitely burn out a capacitor and anytime you set a unit too low causing it to  struggle to keep up (ex. set at 69 but it never drops below 76…) will keep a unit running 24/7.

I’m looking at purchasing an old single family house on a 25x100 property with 25’ of frontage on Summit Ave. in Jersey City’s Heights neighborhood.

You are going to pay top dollar for new construction, but it has several anomalies that will restrict your future value.