RE: Best First guided hunt?
Caribou you can do on your own for cheap! Be it Ak or Canada. Canada is really cheap even on the guided end!
As for what I would recommend, ya ever look into sheep, goats, possibly moose (logistcally speaking more then the diff in cost from a diy to a guided deal, your more apt to do well guided then diy jmho!).
Figure its going to be a once in a life time. Brown/grizzly bears, Mt. Goats, Sheep of any kind, or a 10 day safari in Africa would be neat. Africa would be cool if you can handle hunting behind a fence. Even though the concessions are at times HUGE, it stills irks me wrong. If I did it though I'd be after things like Sable, Kudu, maybe Capebuffalo. Some of the more higher end animals as a regular plains game hunt can be done relativly cheap! (impala, hogs, one big animal to the tune of a kudu, any of the duikar sized critters etc etc).
Just my 2cents, if you are going to pay, go for the gusto while you are capable and willing to do so!