Unless you are confident in estimating the renovations needed, I would highly recommend getting a contractor's professional opinion of the rehab costs.

The risk is too high of losing everything.

The quicker you can take action on the high dollar value decsions the quicker you will be able to grow.For sure take the time to setup the right foundation, but keeping it simple and easy when you are getting going is a safe bet!

Since tax bills are for entire parcels (typically, though not always) then it is highly unlikely that they somehow segregated the taxes for that small portion and paid it.

(Minimal competition, high demand, and 20 year operating history with repeat & longterm clients) Agreed!

Assume my marginal income tax bracket is very high, and mortgage rate is 5.25%.

Our actual carriers used to be Secura, but they seem to be getting out of a lot of insurance lines or pricing so high as to have customers drop off, and we just moved policies in Nov. to Hanover Insurance. 

@Tomas Falcon highly recommend you chat with @Samuel Eddinger!

(in terms of pros and cons).You can also use rentals to provide additional borrowing power if your rental currently cashflows from a tax perspective.Hopefully that helps your scenario advance forward in terms of what to ask and think about.

I set up a meeting with high hopes that this would be a good way to purchase my first few properties of section 8.