With the reading and podcasts, I find elements of all those strategies intriguing but we have to nail down what would serve us best.  

It amazes me how many people simply ignore water problems and live in these houses for years and years and then some poor ole investor comes along not paying attention and gets nailed.

Hey @Nicholas Giordano, I think @Jaysen Medhurst nailed it when he mentioned that CT is a bit more landlord friendly when compared to MA and NY...as liberal as CT can be it does have that much going for it! 

Or if they are walking on your property and step on a nail or trip on a pile of 2x4's BUT if your contractor has insurance than HIS/HER insurance will pay for injury caused by construction type accident.If you have a contractor do work and it causes damage then i.e. roof caves in.

You hit the nail on the head, and that's why I've been strongly considering it.

The nail in the coffin for IIP?

Jake nailed it- who suggested an S corp for holding an appreciating asset? 

Progress pics and city inspections passed to date (continued):Floor framing and insulation complete (both passed inspection)Floor sheathing complete, pending nailing inspection.Walls getting stood up next week, as well as excavation for the upgraded gas line (to feed the additional gas meter) and excavation for the new water line to the ADU. 

@Fred Heller hits the nail right on the head.

Bill nailed the question, the answer you seek is in the comps.