Not sure about your local market but link up with a qualified agent that is an expert in your local market.

I am asking the experts here, where are most of your deals coming from?

The fact the accountant assumed the worst case scenario for you, instead of Letting you know the option and risk of claiming long term cap gains would concern me.

I thought he was going about it all wrong and wanted to find some resources to back my claim, and that's how I came across this website.  

USAA would NOT insure this property due to our "claim history".

You may not find a local CPA who is an expert in real estate tax and accounting AND invests themselves.If you are set on using someone local, I'd look at connecting with a local REIA and asking for referrals there.

Not being an expert in this situation, and this is not legal advice, it sounds like someone made a mistake, and the bank is going to be out that money.

There are plenty of resource you can find under Learn from how to's, blogs from our experts and podcasts. 

What you need to do is determine how you want to policy to react when there is a claim.What do you want the policy to do when you have a $5000 claim? 

Late fees can be claimed in a court of law as part of the Judgment for non payment of rent.