You sound level headed and you seem to have very
realistic expectations. I certainly wasn’t that mature
at your age. I would however suggest hiring several
different escorts for shorter time periods prior to the
big trip.
Since you’ve never hired you don’t even know if you
like the Escort/Client relationship. I started hiring at
a relatively young age (although older than you) and
many of my early hires were awkward because I was
the same age as the escort.
“My money is still good”...yes....and no. You’re still
dealing with humans and all their fucked up emotions.
Nonetheless, I encourage you to explore, do your
homework, hire before the “big event”, and keep your
expectations low.