Here are the rough numbers on one of the houses, both are similar:Total investment (acquisition, remodel, carrying costs) - $200,000Current value (after netting out selling costs) - $270,000Potential Rent - $1,500/monthI can do a refi and get my $200K back out of the project, that leaves me with a mortgage payment of $1,400 including taxes and insurance (assuming 30 yrs. at 5.5%). 

Also, on flood insurance, i'm finding quotes ranging from $600/yr to $1,500/yr but not clear how that works within the different flood zones and asset types.

As a bonus, I just started a new policy this year, that anybody who buys the current year's book always get the next year's ebook at no additional charge, or the next year's hard copy book for $40. 

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.

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.