To answer your question, I would pay maybe three grand to go on a "guided" deer hunt. Not nessessarily a trophy hunt.
There are a number of reasons why I would pay to hunt like that:
First of all, I live in a place where big game tags are drawn in a lottery. Often times you don't get drawn and don't get to hunt big game at all. Furthermore, I use one of my vacation picks at work just in case I get drawn. Then if I don't get drawn, I wasted the vacation pick that I could have used for some other adventure.
Second: I don't live in a place where big game hunting is easy to do. If I get drawn I have to drive 5-6 hours to get to the hunting area my tag allows me to hunt. Then I have to camp there since it is usually far from civilization. After all the work, vacation time, and expense involved in this, it would be nice to have confidence that you are going to have a good chance to harvest an animal. Of course you can greatly increase your odds by scouting the area ahead of time. However, scouting the area requires the same hassles as hunting the area: taking time (at least a couple whole days and nights with the drive), camping there etc. FWIW: the older I get, the less I enjoy camping. I have done a lot of it over the years and now consider it more of a PITA (or back) than fun.
Third: I am not a trophy hunter per se', but like most hunters, I would like to someday bag a bragging size buck. Random chance hasn't worked for me so far.
Fourth: if I was to hunt other states, I have no idea what I am doing. Where can I hunt, local places to eat or stay, where could I camp............. This all involves research and planning which takes time and effort.
Long story even longer, I sometimes think it would be a nice thing to just hop on a plane, or jump in the car and arrive somewhere with the only concern is hunting and not all the logistics of the trip.
I did this on a fishing trip a few years ago. I used to fish in Canada with a group of guys. We would plan the trip on our own. Find float plane pilots or conoe rentals, put all our gear together, fly with all the gear................. Then the guys I was going with got too old for all this and asked if I would be interested in paying a lot more money to go on a trip with a lodge, guides, cooks, etc. I gave it a try and really enjoyed myself. It as probably the best trip I ever went on. Doing the same thing for a hunting trip would probably turn out the same way.