Sounds like you aren't yet sure what you're looking to get out of your boat. I would suggest buying an old 14/9.9 rig on a trailer (dime a dozen on kijiji) and get a feel for what you like and don't like about it, and more importantly get familiar with the level of maintenance required to keep a rig in tip-top shape (likely more than you think if you e never owned one before).
The big things you need to know when looking at a used unit is seeing the motor run (ask about lower unit seals and impeller, gear oil etc), compression tester if you have one, age and condition of trailer bearings, tires, leaky rivets. You'll get a good idea from how the seller responds as to how well the boat was taken care of.