I think you’re headed in the right direction if you want to have a quality fishing experience with less expense.
Canoe? Yes
Kayaks? Yes
14'-16' Jon boat with a trailer? 16’ would be better than 14’. Running a Prop motor would limit your ability to cover much water. A jet would open up much more water and opertunities.
How big of a jet rig to fish 2, maybe 2 and a boy in comfort and safety? A matter of experience and opinion. See “guys using” response below.
1752 with a 60/40? See “guys using” response below.
16' with a 30/20? See “guys using” response below.
What are you guys using? Royalex Canoes for headwater floats and when traffic permits a white river john for main stem rivers.
Where are the best stretches of river? All the best bass fishing opertunities in the Meramec basin are within a one day trip distance from you, I’d fish all of it. Sorry for being so general but it’s kind of true. Some years some stretches of river will fish better than others. Sometimes you can have mediocre fishing on the best stretches and other times the best fishing on the mediocre stretches, you'll never know until you spend a bunch of time finding out, thats the best part.
I work most weekends, so this is pretty much an early morning/evening operation on my days off that I'm thinking about here. (Monday and tuesday) Perfect.
What about Simpson lake, creve cour lake? Worth dropping a glass boat in and using the troller to kill a few hours and catch a couple bass? Mud holes, you would need to be pretty desperate to invest much time on either.
Going through past forum post will provide more information about local fishing than a person could possibly digest.
Good Luck,
Give us a report when you get into some fish.