First, what's needed to satisfy any outstanding mortgages.

If so, concentrate on lowering those outstanding balances.

The weird part is that the tax search website did not show a lien or pre-forclosure or any foreclosure history on the property and 99% of the time when a loan is in default I can see that.After searching the Dep. of Finance I also found that the taxes have not been paid for over a year and are still outstanding. 

The longer you have the loan outstanding the worse the tax/performance impacts on your retirement.

Some plans will not let you contribute to a plan while you have an outstanding loan.  

It's underwater, and total outstanding debt is $300k.A few things I'm wondering:Was the $140k starting bid at auction just a teaser rate and the reserve would have been much higher?

I used to manage a 200-men crew operations, a crushing plant and 50ish truck/equipment fleet management for a family owned business, it was all self-performed and no subs are hired, anyway, I will keep things on the construction side.

Why dont you get a heloc and pay off your other outstanding debt?

I run a fleet of 10 trucks, and since they are all over the IRS gvw weight limit I can depreciate them up front.

As another side note, you best keep an eye on those outstanding tax certificates as they at a point where they can petition for a tax foreclosure for lack of payment.