Upload & Sell: Off
Frankly even $200-300 is way high for me. I was thinking along the lines of $50-75. Maybe $100 tops, maybe. That should cover his reg fees for the past few years and then some profit on top of that. Doesn't help that one iteration of this domain is openly for sale on sedo for less than $100. If asking these domain owners for the TLDs I want doesn't work out I may just buy the one on sedo.
IMHO, the domain is pretty much worthless except for perhaps a one in a million prospect. What it has going for it is that it is short. However, it is not composed entirely of "premium" letters, is not really pronounceable, is not similar in any way to an already existing well-known acronym or company name, gets all of zero hits per month in type-in or misdirected traffic (or at least so little that it is not recorded by any traffic aggregator), etc. Based on my research, people who invest in domains would likely not pay more than $20-30 for this domain because it lacks a lot of key "value" features. As such, I feel $50-75 is more than fair considering I am that one in a million guy who actually wants to use it.
I sent the domain owner an email asking if he is willing to sell. I was torn whether or not to put a starting price in the email (I ended up not including one) because I feel if I went in with my planned opening bid of $50 he would likely write me off immediately. I dunno though, it's really hard for me to figure this stuff out. I tried to "case" the guy out (kind of creepy- you'd be surprised at what you can dig up about someone with a little internet searching), it does not seem like he is a serious domain hoarder- some cursory research suggests he only owns like 10-15 domains, so likely using most of them for actual websites, and not hoarding them for profit. I am hoping this makes him more open to selling at a reasonable cost. I do know now that he is a bit of a photog himself though, shoots canon, and owns at least a couple L lenses . Maybe I can work that angle hehe.