If emotional attachment is an issue, or if the move is unwanted but necessary, the sellers agent might be able to speak to some of that, provided they seller has given permission.  

Am I being penny wise and pound foolish?

If you don’t know someone who uses a shredding service, you can bring a pile of receipts to Office Depot for a few dollars a pound and they’ll do it.

Or at least tell him to pound sand and that you'll buy his property the proper way and now that you know what you know his real price to you will be $440K."

I thought about the "natural" approach but know little that I do, I'm sure they can catch on that I would be seeking the knowledge they have experienced, by my series of questions.I don't want to come off creepy or unwanted while searching.

I dont recommend others take this kind of risk because I was nervous, but they, pound for pound have been the 100 percent best tenants I've had in any class property I have owned.   

You've either got to pound the pavement HARD or have a solid marketing budget to get any traction down here.

Seems like a massive amount of risk inheriting a tenant to try and keep their $500... that $500 will be nothing in the grand scheme of owning a property and I would have gladly given that up (if you even get to keep it in the end) for someone to remove an unwanted tenant.

I have heard the same thing about apartment owners & managers compiling a list of unwanted evicted tenants and have run into some issues with doing this.

Are you okay with appliances being on the person's porch and cars on blocks in the yard or do you have rules that no aggressive dog breeds more than 30 pounds are allowed.