@Caleb Heimsoth You are correct that I haven't asked a lot of real estate investors (I have asked a couple, but they believe they wouldn't qualify).

I was looking at 350k worth of properties which would leave 65k to be taxed if im understanding it correctly.

If you're buying much quicker than that, I fear you might not have had enough time to do enough due diligence.The problem with your current method is that it leaves no room for error and is dependent on everything going right. 

Chris Gordon Cash on cash is only one metric which is not the correct metric for long term buy and hold.

You are correct, the points are on the entire loan.

I am not a CPA, so check with yours first, but I believe you are able to file a forms 3115 and 481a (change of method of accounting) which allow you to claim previous year's depreciation without actually amending previous years tax returns. 

Cameron Elliott Wayne Brooks is 100% correct.

I know a lot of big owners that are sitting on a ton of cash and waiting for a correction.

I want sufficient insurance, but if something catastrophic were to happen I would construct under more modern building methods.

I know looking back on houses we've sold, they can have several different sales prices, and none of them are correct.