The home is unique in that it is connected to a studio apartment, which I had intended to set up and run as an Airbnb listing.

Our adjusted mortgage payment is then based on these numbers:$137,500 "purchase"$41,250 not liquid and left in property (30% of home value)$96,250 pulled out and liquid on a stabilized assetConclusion(Not accounting for any closing costs):We have $71,250 in liquid funds after repaying HelocWe have $46,250 in liquid funds after repaying our bank account for the initial downpaymentWe also have an asset working on the numbers in the analysis below. 

I found myself in a unique situation- I had a general direction in which I wanted to do my first investment.

“But this case was unique.

If you have made a living as REI and don't truly enjoy the unique community here, then you don't need BP.

Most hard money lenders shy away from owner occupied properties because they subject to ATR rules (Ability to repay).Traditional financing through a lender is not available on a property that is being publicly auctioned.

1) Make a unique monthly budget, discuss it, and stick to it. 

If the house goes to foreclosure, then the winning bidder needs to repay all my costs, except the servicing fee, plus the remaining note. 

I understand this is a bit of a unique but I'm not trying to scam my family.

I think your problem is that USAA doesn't offer any products that account for the unique risks associated with bed and breakfast/ short term rental businesses.