"Love of the game" has got to be the most overused colloquialism in sports, not just disc golf. If you want to "love" the game, then stay out of serious competitive events. The idea of a competitive events is to win, and when said events have a serious price tag attached, love can get to be rather expensive when your skills aren't up to par.
And I've said it before every time this subject has came up in the past, and will say it again. Wins, particularly wins in any division but open, don't mean jackity jack, when considering if its time to move up. Different tournaments bring out different competition and that little variable, one a player has absolutely no control over, can have a dramatic effect on whether you win or not.
What you should consider, when it is a fair comparison to do so (as in, you played the same courses as the division above you) is how you would have finished had you played up. If you find yourself being consistently competitive (not necessarily cashing, but definitely finishing in the middle third), perhaps its time. If you find yourself doing it occasionally, perhaps you should do it occasionally (namely when the price tag is cheap). If you find yourself in deep donator range almost constantly, I'd suggest staying down, unless you signed up more for the experience of playing at that level.
I know a number of players who do just that, repeatedly, and often with the same results. Who am I to say that they're wrong to swim with the sharks. Its their money.