If the leak is due to the software I would switch to a bigger more national brand instead of some company that is smaller and has the ability to have cyber issues.

Have bought, renovated, refinanced and sold rentals in my portfolio.Besides monthly cashflow, you can cashout refi every 5-10 years or when increasing rents support the ability to do so. 

This can become a risk for both you and your ability to sell.As for things to talk to HOA about, beyond the permanent exterior colors/finishes, I would also ask about things like dumpsters and potentially port-o-let's that may be needed during rehab.  

Hide you money, drugs and valuables off site.If you do your own opens, do it for a couple of weekends.Once you have someone interested, you fill out a purchase & sale agreement, collect an EMD, open escrow, order title, verify ability to close with the buyer's lender.

Will they lose their ability to deduct bonus depreciation against their regular 9-5 income for all future years?

Welcome to BP - rates have finally come down a bit so that cash flow is now possible again in some markets for classic turnkey rentals but still have a bit of a ways to go - if you have the ability to BRRRR - that is going to likely really be the better strategy to get a more robust cash flow at the start

If you are charging market rent, the rent you will lose for that 1 week of occupancy would afford you the ability to rent a comparable property on the market without the need for any of this kind of nonsense. 

This is a very difficult business with dozens of moving parts that need to be managed and mitigated through expertise and ability.

You can ALWAYS negotiate if both parties want to and with you having the option to back out of the deal you have the ability to leverage the seller into "wanting" to negotiate. 

Early on in this discussion I thought you were just a wide eyed fellow taken in by the ability to enter into a market with little investment.