Contractors will make or break your rehab. 2. get 3 quotes for everything. 3. closing costs for refinancing is not cheap and you definitely need to take that into consideration when running your numbers. 

Scaling well can make things more interesting, but putting good people around you would definitely help. 

Would love to come, I’ll be out of town that week but the next one I will definitely try to make it! 

Except one thing...2nd: Refinancing isn't free (usually, unless your broker factors it into the rate they're giving you and then it's definitely not "free").

I'm contacted weekly from reference senior positions and contract work with the government, but I definitely enjoy the time with my brothers for the last few years before I hopefully retire for good. 

An older home you'll definitely know if there's a foundational issue or not.

It is definitely not "passive", but it is still a great investment vehicle.   

Sure thing and it's definitely true that the problem with asking others opinions is they often disagree with each other and there's a lot to sort through.

Its definitely a big cost/premium risk allocation discussion

If you have property in CT, I would definitely give here a call and keep her on your PM list.