I lived in Sound End for a bit; beautiful, walkable area with plently to do 

Sounds like he's had a ton of experience as well.

Does this sound right?

Ditto @Michael Baum - a simple 3 ring binder and I update/replace it if it looks even a bit worn down.

Since reserve studies attempt to forecast replacement costs of items over a 30 year period they are having to recalibrate since the reserves they are now using did not use the latest increase in construction costs.

We've owned them for 20-plus years but the recent property tax increases have negatively impacted our cash flow as have major repairs such as roof replacements, AC units, etc.

The GP was so open and transparent every step of the way with the different types of insurance that were essential, adjusters, replacement cost, debris removal, code upgrade, etc.

I know, it sounds good, but in most cases, if it sounds too good, it probably is. 

It sounds like your house hack was a success after securing the FHA loan and renting out the second unit. 

It may sound nice to pay a 6% management fee but the extra fees can add up to be more than the other company that charges 10% with no additional fees.