2.Does anyone have experience investing in or house hacking in Danbury?

I run a MTR out of my primary bedroom and would be happy to connect and chat about your plans and what my experiences have been. 

I manage around 400 rentals with 14 years of experience and have never been sued once.

Do you have prior experience to operating the rehab credit contingency to avoid the seasoning period?

I made the mistake of letting someone get in one of my first units that was a bit off the 3 times, they were great tenants very kind and enjoyed their stay and experience with me, but could not afford it when I increased the rent on them, which is something you will have to do because of rising insurance/tax costs.5.)

Your decades of experience have made you jaded. 

Definitely continue seeking advice from experience realtors and understand your rental market, and make sure you understand the risks involved.

It also gave me the chance to experiment with short-term rentals before transitioning to a long-term hold, reinforcing my strategy for growing a real estate portfolio.

Just to clarify, when I say timeline dates I don't mean just "project to be completed by (Date)"That's required by FHA/Lender, but in my 20 years of construction experience not nearly what you need haha. 

Sounds like you’ve got some solid experience under your belt.