He wrecked it and didn’t want to claim it on insurance.

@Ken Domond  Generally speaking abandoned boarded up wrecks will be difficult to turn around in a full gut rehab ... very often you can buy existing product for cheaper than you can rehab. there are exceptions to this..

I paid about $8K out of my line of credit to just buy my friend a new trailer to replace the one I wrecked, and a little over $3K for towing from the wreck site, and towing it home, and don't forget $5K of shingles. 

I also used a DTI calculator to ensure I wouldn't over-borrow and wreck my credit score.

I am currently doing a refi for a rental property I just bought earlier this year with FOA commercial and it is extremely nerve wrecking. 

But for most of us mere mortals, a $50k or $150k loss on a property would wreck our finances (if not ruin our lives completely), so we pay a relatively small percentage of that to pass that risk on to an insurance company.I suspect the reason your neurosurgeon friends don't carry insurance is they can afford not to.

This applicant sounds like a Train~Wreck to me.

I only recently got into the game here in Boulder.The HOA for that condo complex is a train wreck.  

Bottom line was it was going to be a train wreck whether I raised the rent or not.The question you have to ask yourself is would you select the tenant as a source for your charity if she were not in the property you just purchased?

If we are talking about rental property, I buy the cheapest: switch & plate covers, mini blinds (even expensive ones get wrecked), toilet paper holders, etc.