Iḿ focused on passing down a functioning business that I assume will be sold for the wealth.

First, we invested $25,000 in targeted repairs and renovations to enhance the property's appeal and functionality.

These were mostly pretty high functioning offenders who just had slightly lower IQs and in some cases likely were just poor test takers in school.

Biggest issue is the tax, its much higher than anticipated 50k as w depreciation recapture is 81k after i paid 5800 transfer tax at closing.. so thats a BIG problem and i want to make sure i pay minimum on that - use 10-20k upgrades i put in prior to selling, max out LLC this year to write all expenses off from it etc. - Any advice on how to offset that 80k tax?

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

We don’t mind the recording process—at the very least it’s a tax write off—but let me throw a few more angles out there that I hadn’t mentioned before and see what you and @Chris Seveney think: the CFD’s we’re purchasing are for unimproved land parcels, so I don’t think there’s an obligation to insure.

Who cares what you did as a kid, or where you work now, just a waste of time writing. 

Prepare yourself now.Give the property manager notice in writing and at least 30 days to prepare for the transfer.

Yes your Heloc + Mortgage for the first home will be added to your DTI, however if you have a tenant in place that covers that amount (contract for at least 12 monhts) you might be able to write it off... 

If they are OK with it, put it in writing so they can't change their mind later.