So my wife and I have wondered, a) should we try and buy the most expensive house we can (that's still an asset producer) with the lease money down, so that we can later sale those for the most cash and use that money to buy more rentals.  

We only ask for the first 1 or 2 pages of their past three months of bank statements and we ask to see copies of their checks or some type of verifiable transaction where they paid their rent on-time for the past 3 months.Renters can some big liars and they know how to produce fake copies of receipts and say they either lived with someone else, or they paid their rent with cash.

I liked being a mediocre Marine because it allowed me thr freedom to get in a bit of trouble.

That's seems like a lot of trouble since claiming a house and then unclaiming it really complicates your taxes and life in general. 

We have a property that has been label high risk and as we have claims in the past couple years all due to natural disaster that hit Des Moines, IA ( storms )Current policy has been cancel and having troubles getting new policy.

I usually sort of "hack" the rental calc to make my STR analysis work out for a yearly average.The big thing I'm having trouble finding help with is something more geared toward development. 

Since I am new I'm not sure what trouble I will have to go to to "prove" this is causing the damage.

You have the best of both world--an appreciation asset that is also producing income.

I know that it's not scalable, but that's one of the areas I have trouble giving up control of my business. 

Cleveland is great, but since the pricing is so cheap investors sometimes put blinders on and get themselves into trouble by not doing their proper due diligence.