The IRS sees that you always were engaging in an active business activity and the holding time was just an attempt at circumventing the tax liability, which they will disallow.The general advice given by the tax professionals (of which I am not one so seek your own counsel) is to keep different activities separate.

I am attempting to jump in head first without cracking my skull :/.

I wouldnt jump to conclusions and go spending money to fix anything before attempting to narrow the problem down.

Heck, just the awareness by a contractor that the agreement/contract was memorialized via audio, may in and of itself be reason for a contractor to "perform" instead of digging his heels in and posturing in an attempt to change the terms of the agreement at "crunch time", or worse, not performing and then seeking redress through small claims court, mechanics lien extortion or who knows what. 

Attempts to get info from the company don't get returned.

What you witnessed was my failed attempt at humor.Also I misquoted the quote you quoted me on.

I'll be traveling a couple hours out of my area in an attempt to find investment friendly neighborhoods.

I am also going to study real estate markets in Iowa in an attempt to locate a the right market for me to move to when I get back home.I have found that a focused effort is much more effective than blindly throwing darts.

Can I still attempt title insurance to make sure there are no other liens or does the sheriff's deed imply that those were eliminated?

I’m kind of new to real estate investing and attempting to learn as much as I can before making another purchase.