Go with what you need now . . .
You may eventually wind up with a pair of SOTs and touring kayaks (sit insides). We have both and use them to advantage, based on conditions:
Warm weather: SOTs or Touring, depending upon how we are using them. If we want to cover a lot of water (eventually, we will do some light expedition touring) in a shorter time, we use the touring boats. If fishing, getting off and on a lot (for stops, difficult docking, etc.) free-diving with snorkeling gear, we use the SOTs.
If you tend to have sore joints and muscles that may make boarding a sit-in difficult, an SOT may be ideal. When I’m sore, I use the SOT.
On our rocky NC rivers, we use the SOTs; on the sandy rivers in Florida, we have tended to use the touring boats - although, on the present trip, we took the SOTs.
When the weather is cooler/cold, we take the touring boats.
Consider emergency options: Use of touring boats will require more early development and practice of rescue skills (T-rescues, rolls, etc.) and you will need to be able to re-enter your touring boat if you venture from proximity to land. (It goes without saying, your touring boat needs bulkheads for flotation.)
If you dump your SOT, you simply flip it back over and crawl back on, so there will be less need for early complicated skills development. Remember, that your joints and muscles should not overly limit your capacity to deal with emergencies, like re-entry, and your choice of a kayak type should reflect your limitations as well as your potentials.
There are variations: there are some long and fairly fast SOTs out there and some sit-insides (rec boats) can be wider and slower than some SOTs.
So, figure out what kind of paddling you will do, where you will mostly do it and during what kinds of temperatures. These, along with your potential for skills development will play major parts in whether you go SIS or SOT.
Finally, consider what issues you may be facing with respect to your ability to deal with weight. Generally, touring boats are lighter; SOTs can be significantly heavier - requiring special car racking and carts to move them to the water - especially if you have fishing/diving gear.
One other unusual question about SOTs versus cockpit kayaks was brought to me yesterday. We had just pulled our SOTs out of the Silver River, near Ocala, when a guy asked me which boat would be safer around alligators - an SOT or one with a cockpit. I couldn’t come up with a definite answer, except that there would be trade-offs . . . maybe the kayak that least resembled an alligator would be the safest.
But not to worry, I told him. The ranger had told us the river only had gators up to a couple feet - and we had not even seen one gator during our paddle.
“Oh really?!!” he replied. He pulled out his camera and displayed a bunch of photos and video of a number of gators he had just filmed - some over 10 feet long. (Damn, what was that ranger thinking!) So, now, I am mulling over that final question myself.
