Their ability to help you is limited if you go after. 

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. 

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.

I'm trying to determine which platform I want to use going forward to start this side business.

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.

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

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.  

I estimate each task to the best of my ability and then I estimate my ability itself.

When you apply for a refinance, the lender will order an appraisal to determine the value. 

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