For a target like this where it is abutting an airport, you could be negotiating with the seller that it would be a more difficult exit strategy later for you and if they are motivated to sell, they will come down. 

Aside from predicting the future, how can I change my process so that these letters come in a more timely fashion?

I'd also toss in that you want to take a more active role in the community and that him selling this to you give you that chance.Sounds to me like this guy is going to value time and sense of community over dollars and cents...

Or is there a more critical change in the market that I'm missing. 

My question is do I need a more extensive of insurance policy with people staying on our property.  

We found a more competitive guy and we're going to see how that goes.  600 to hang the bottom 4' in both houses and 1800.00 each to tape, float, texture and do the trim-out. 

He's offering to transfer ownership of it for $500, but I can get a more generic domain for $20.

You really need to do a more detailed analysis of your income and expenses.

Where the OP may find this kind of deal is moving into a more rural area just outside of those midsize cities. 

In case it is a single member the taxes are done on your personal return.If you want a more professional treatment I suggest you contact Borders and Borders real Estate Attorneys.