@Timothy RileyYou have a solid plan there friend, I like the way that you mitigate your risk and you obviously have multiple exit strategies in place.

I know how to mitigate most of the risks!

This additional risk and volatility can be mitigated, hedged, and/or completely avoided by a skilled REI operator, but if you are not there yet then it is a decision of growth vs. safety in my mind.

A lot of people will argue the increased risk of losing money from inexperience in this endeavor - while this may be true, I am not clear how paying at or above retail on a property mitigates the loss of revenue from inexperience, as you absolutely can not put a price on experience.    

Agreed, if you need to slightly overpay (a couple of thousand dollars), if there are mitigating circumstances, ie huge cash flow, or in the path to progress, thats one thing. 

@Alex Corral There is no one right way to do this.What matters is that your logic makes sense to you and that it mitigates the risks that you perceive in each investment. 

Even though you can make a list of things that mitigate your risk and increase your odds of success- you are still gambling. 

Just my perspective - One can do three things to manage risk - mitigate, accept and transfer. 

How to mitigate those risks?

I know these options aren't available to everybody, but to sell whole life insurance as the only tax mitigation strategy is baloney.Thirdly, my father-in-law certainly isn't a financial moron, but I don't think he's right about whole life insurance.