If anything, you'll get an additional tax filing and a reduction of your lifetime exemption.

Two of the buyers came back with 2k less in closing costs, while the other offered 152k with no reduction in closing costs.

Ask the dumpster company how much weight comes "for free" with the dumpster, and what the cost per ton is for going over that weight. 

Those properties are assessed at 4% ( a 33% reduction) and are exempt from paying school operating cost (about another 1/3 in savings.

Same here - my CPA seems to think that loan reduction boot is considered as "ordinary income".

Bulk up the porch columns to give them more weight.

I will tell you that those nerves are normal and it means you are thinking carefully about the decision and understand its weight. 

... also, regarding you getting a loan with this proposed purchase: the credit of the IRA account owner would not be of weight here, the loan must be non-recourse, the IRA account owner can not personally guarantee this loan. 

My specific question for experienced landlords is: Do you ignore or put less weight in medical collections as opposed to other types of collections?

Would you negotiate for cash back or a price reduction?