Read and understand the paperwork,then make sure if the worst happens you have reserves or alternatives in place so you are not in deep water.

If not owner financing, you need to check alternative lenders.    

Alternatively, if there is a way to add a bathroom on the second floor - it would be a good deal. 

In the news: Not an 'alternative fact' but an actual fact.

I'm also curious to learn about any other sort of private and/or alternative financing that may work well with my scenario.While I don't yet know what my 10-, or even 5-year plan is, the idea of pursuing REI as an escape from the "rat race" is very appealing to me.

I am a big advocate of developing long-term systems and habits that make wealth-building second nature.

I think transparency is key here -- if the VA lender knows the nature of the transaction, and agrees to not fund until they are presented with clear and updated title reflecting that the ownership has been conveyed to the wholesaler, then a double closing could still be possible.I must stress that I am not an attorney nor a realtor nor a licensed closing agent in Colorado.

As a fairly stoic Boglehead by nature (passive, low cost indexing), I've had my doubts as to the efficacy of REI for stable, long term financial readiness due to a perceived "impossibly high cost of entry" for the community and my lack of knowledge. 

Expenses are too high and net profit too low for lenders.You would have to find alternative financing sources if you can't find a local lender looking to support your deal.

Your cash out refinance is a good alternative, but what if you don't need the money right this second?