Some really nice comments. Ryan, nice post and would like to hear from you more often!
Considering Terry's situation on the Kish and Kilbuck, a smaller sit-in is very affordable, lightweight, easy to load / unload and transport. You can drop in just about anwhere with ease and enjoy the boat. Perfect for hit-and-run type fishing and exploring small waters. Leave the waders at home. Keep stealth and stay in the kayak. Some slop boots are perfect for shallow put-in / take-out and you're done. Easy on your budget without all the bells and whistles marketed towards anglers -- most of which are "nice to haves" but rarely "must haves."
Sit on tops are nice and comfy but there is also added weight to lift and push. You're also higher and if it's windy, it can be tough.
Your budget is going to determine a lot. I think a 10.5' sit-in between $500 - $700 is enough for most situations around here. Also consider the cost of any additional equipment needed for transport, storage, a life vest, paddle and anchor.
It's always good to test paddle before you buy. See what feels comfortable, especially if you have any back issues. You might rule-in / rule-out either style quickly. The best boat is the one you'll actually use!