Personally, I would hang on to the cash.  

I’m not a former IRS person.

I warn people over and over and over to know what they are buying and to go personally see what they are buying. 

I tried to create rapport with the owner over the phone but waited to present my real agenda only in person.   

Not talking about you personally.

I would spend money to enhance and update to current standards the search functionality and person to person tagging so it's easier to find stuff.

Dumb question - but are these auctions online only, or in-person? 

I've done enough personal home projects to know, if I find a deck company it'll be 2k, but a GC will charge me 2.5k to over see it...

Personally, If I could pull out a HELOC, I would use it to fix and flip which will typically make sense as you shouldnt be keeping the money out for that long and you can recycle it or pay it back and build off the capital that you got from. the flip.

The cost to repair your vehicle, and perhaps the other person's car, will be WAY MORE than the cost of the insurance premiums you saved by not having insurance.