I understand that a single 60 is unlikely to get the boat on plane,
You sure about that? No first-hand familiarity with the Tolman hull design but I have seen some damn big hulls moved around nicely by single, small-displacement two strokes.
There's a place where we hunt where guys run open aluminum scows ranging from 20-24 feet for trotlining and eel netting. They all run Yam C40s and don't have any trouble planing, they are just slow.
Same token I have seen more than a few Lund 20s with 50 hp motors -- a few dealers like to sell 'em that way to guys who can't also afford a nice new 115. I don't think it'll carry much of a load but they do plane out.
Tolman would be a lot heavier and draggier but still, bigger boats than that have been planed with a single, midrange outboard.
Here's some more food for thought: for what you want to do the old four-vs.two-stroke debate might actually be meaningful. I'm just picking Yam because I'm most familiar with their products:
The Yamaha f60 four stroke is 237 lbs., times two is 474.
The Yamaha two-stroke 70 is 228 lb.; total weight would be 18lb. LESS than twin f60 four strokes.
And having run both the f60 and the 70TRX on identical boats, I can report that the 70 TRX has a LOT more balls than the f60, all out of proportion to what looks like a relatively modest increase in rated hp. Burns a lot more gas, too, but it's a stone reliable motor if you take care of it.
Move up the scale even further, the Yamaha two-stroke 90 is 261; total weight compared to the f60 would be 48 lb. more, but I bet 50 extra pounds off the stern of a 22' boat won't mean too much, and then you would have more confidence to move the boat decently with just one motor, without fear of lugging it at low rpms (and grenading under the strain).
As to your last question, I have run a Lund 18 with a kicker (8 hp) in poor weather, just to see how it would do. I didn't really like it. I could keep it from wallowing in the trough just fine, I could heave to without dying, but i did NOT trust its ability to bring the head up into a big sea. Based on that (limited) test, I have never since carried a kicker as its extra weight, inconvenience, and risk of it getting me halfway out of a jam outweigh its benefits for me.