So, guessing you are in south or southeast WI.
Lived in tosa, Milw, Brookfield, for 35 years, now I'm further north.
Just driving an hour or more away from the huddled masses came make your day on the water so much more relaxing.
Koshkonong, Lake Mills, Beaver Dam, Fox Lake, then a bit further up the Wisconsin River is Castle Rock Lake, and Petenwell Flowage. And as you know, lots of good water in the WI River.
Makes and models? way too many to consider.
Your price range should put you in a fairly new boat, but don't be afraid to look at a boat that is 14-20 years old.
Condition is more important than age.
Get it inspected by a mechanic before buying it.
And get an on water test drive with the seller if possible.
Make sure you get current registration and title for the boat.
And current registration for the trailer.
Make sure they are all in the sellers name.
If you go with an i/o, then only Mercruiser engine and outdrive.
For outboards, Mercury, Yamaha, Honda, Evinrude E-tec
What to avoid?
NO OMC, Force, Ford, or Ficht.
How many people will be in the boat?