I would say given your initial budget buying a used boat with Jet drives is not a good Idea if your not 100% ready to do your own maintenance...
I didn't look for a poll but I'll bet the majority of the folks here that put any hours on their boat do at least some of their own maintenance...
for me I moved to the Keys and had a list of requirements from Rear Adm. Lower Half Blond Beach Barbie:
Sufficient Beer cooler capacity
RED
High FreeBoard (dont want to fall out)
Good Sound system
place to lay out in the sun
easy in and out of the water
BBQ Grille
My requirements were:
<10K
daily use capable
Jet drive
reasonably fast
shallow draft
sound system
stripper pole
Im still sneaking up on it but Im down to just the stripper pole LOL (this place is a bad influence)