As we started to rip flooring up we uncovered other problems etc. 

With a little extra effort, you may uncover something that would steer you away no matter how good the price.3) What do I have to offer (outside of $$$)?

Your contractors may uncover some additional repairs that are needed that they might have seen when they first gave you the estimate. 

Did you get a pre-inspection to uncover any issues or did you wait until after it was under contract?

My accountant may have a heart attack at the prospect :) Has anyone run into problems with the IRS or their CPA due to moving blended cash flow through one HELOC? 

You may have already uncovered this in your research, but should you choose to invest in Chicago, you will be tempted with the double digit cap rates and high returns with properties on the south side of the city.

Lastly, as you can see from the pics we uncovered the original cedar shake siding which is in excellent shape.

If there is something that the appraisal will uncover then you might lose your EMD. 

I understand it varies by county but I assume I can just contact the county via phone, email, or online portal.Do you know of examples of what an official title search could uncover that I'm likely to miss?

I just read all the BP posts I could find related to the Section 121 exclusion ($250k/$500k capital gains on primary residence) and I uncovered two issues that make me want to sell our AK house soon.#1:   I can only use the 121 exclusion once every 2 years.