Would you just “low ball” him an offer, knowing that might upset him and either have him so ticked off, he walks, or maybe he angrily counters with some astronomical number?

If you want to sublet, be prepared for an upset landlord when they find out, they will be even more upset if they pay for electricity and learn that you are mining crypto-currency large scale. 

They would rather loose 2-3% of a 50k differential rather then upset the seller or delay a sale with a big price reduction.  

I'd be more upset about that fee than anything you paid on the loan.

Do people get upset if you call too late during the evenings?  

She got so upset that the following year she did not renew the lease!

The other factor is when someone scratches or dents my car as happened last year I wasnt all that upset by it..

the biggest problem with wholesalers in my area is they never tell the sellers what they are actually doing and then if they cant find a buyer they just bail out leaving the seller very upset @Brian Gibbons

My agent was upset at me for going over his head and told me it is inappropriate to talk to the selling parties.I think that had we used the correct purchase contract in the beginning though, with the clause that requires the seller to produce the records in question, all this drama would have been avoided. 

I guess I was more upset that I drove all that way just for the guy to call me 23 minutes past our appointment time, to tell me they changed their mind about selling.