You'll just need to find the balance of giving amazing and caring customer service to those sellers in need along with remembering as an investor, you are a business and you will need to create a win win situation for both you and the seller.

But things get more complicated when a lot of these people renting out their basements illegally are also not paying taxes on the income... and then theres Insurance & liabilIty Issues as well. anyways, I personally am trying to find a way to do things as legally as possible.

I want to pay for future customers. 

At $89k ask, there are $5,500 in closing costs ($1,500 of that is tax prorations) and then $2,100 in prepaids (insurance/taxes).

@William Larson Make sure your insurance policy covers your complete annual rental loss.

How did you research and evaluate those "costs" of leaving the corporate world, how did you find health insurance for you and your family, etc? 

The bank will find out when the insurance policy is updated. 

It sounds like any other sale, even though it is being done by auction.  90 days is Plenty of time to get financed, but you’d have to make sure:It’s zoned as residentialIt will appraise for your bid priceYou can have access for insurance and lender inspections/appraisals.It is in good enough condition to get a conventional loan, or you could take a shot at a 203k or Fannie purchase/Reno loan.The auction terms/details Should tell you if this is prohibited for some reason.  

I'm not even sure how this would work since the insurance company is paying HH and HH would be paying me.  

Typically, borrowers must provide title insurance policies to protect the lenders' monetary interests.