I think I'd like to get into this. Canoe seems like the way to go, because I could take the kids or dog or tent and cooler along. On the other hand 90% of the time I would probably be alone, making kayak the answer. So how hard is it to drive a canoe when you're alone? I did a little (very little) canoeing when i was a kid. Ive never been in a kayak. I know almost nothing. Teach me.
Kayaks are fast. As long as they're in their element - a whitewater boat is a bit slow on the flat. A real sea kayak is a joy to paddle because they just glide through the water. However, kids and dogs and coolers are definitely not an option. Tents, no problem. The flatwater boats are easy to use and steer and quite stable - takes a lot of effort to flip a sea kayak, and even more to roll it back up again.
Solo canoeing is a lot of fun, but it's not easy to do well. It's about as fast as a whitewater kayak on a lake, but you've got some really interesting moves and there's something zen about it. I've got many hours in both modes of transport and I'll use a kayak when I want to get somewhere and a solo canoe when I want to just play around or go for a dawn paddle.
If you're thinking you want to try it, rent a boat for a weekend.
Canoeing is not hard alone. You just have to switch back and forth a lot.
Kayaking is generally less about "driving" and more about "steering". It's made for white waters, while the canoe is made for still (or slower moving) water.
I've lost my nerve a bit on kayaking. My uncle was a world class kayaker and died in a still water accident. I also had a white water incident last year that was a bit too close for comfort.
Canoeing is more my speed. 
I kayak and SUP frequently since I live on the water. I occasionally borrow my neighbor's 17' canoe if I need to take someone with me or need it to use as a work platform to do dock or boat lift repairs. I don't find the canoe hard to handle alone, but I've only taken it maybe a half mile alone.
I loved kayaking until I got my SUP. Now I like that better for tooling around/exercise than the kayak, but I still use the kayak for collecting trash from the marsh since it is easier to carry cargo than the paddle board.
Stand Up Paddleboards (SUP) are all the rage these days. From what I understand you can get a decent inflatable SUP for a few bills and they are pretty compact when deflated.
Me? I'm looking for a good option that would allow me to learn the basics of sailing while still being a decent paddler.
If you're having to switch back and forth when solo canoeing, you need to work on your j-stroke 
SUPs are okay. They're the result of a dare to develop the least efficient and most unstable method of traveling over the surface of the water. The inflatable ones are slugs, a hard shell is better but still not quick. I've got one of those as well. They're good for puddling around on a lake and for playing around, but they don't have the grace of a solo canoe.
There are a bunch of variations on kayaks. There's the Cabela's style which is slow but easy to handle. Some have you sitting on top, some have a big cockpit. Good choice if you don't expect to get out of sight of the dock. The equivalent of a Crown Victoria. Or a Camry. My parents have one of this sort of breed at their cottage.
Then there's a whitewater boat, which is enormous fun when combined with big rapids. This is not what you want for starting out unless you have access to the right water. It's the stripped out V8 Miata of the kayak world. Huge fun if you have the water, but also the best opportunity for injury. Get a bombproof roll going and you'd be amazed at what you can do with one of these.
Then there are sea kayaks, which are the Grand Touring boats. Let's say Aston Martin or big Mercedes. Made for serious distance and travel. I've taken these on multi-day trips and love them for it. They're very stable in a straight line and usually have foot-operated rudders.
I think the SUP thing might get a little crowded once I put my eight year old son and 70 pound labramutt on there with me.
If that's even a possibility, then only the canoe works for you. Although I saw some inflatable SUPs in the outdoor store yesterday that were basically floating docks. You could put a lawn chair on them.
I'm a huge fan of sit on top sea kayaks. Missing out on the past 2 seasons has bummed me out quite a bit. They make an excellent fishing and touring platform.
Single person canoeing gets interesting if you get any wind, you simply won't be able to tack across in certain directions and will be very limited regarding where you can go. With no wind you're fine, above 15mph, you're sailing.
The choice of canoe makes a difference there. We've got a big cargo canoe in the family that is a brute in any sort of wind. There's also a 16' cedar Chestnut that does okay in the wind, although 15 mph is a hassle in most paddlesports.
It's really interesting to see what "canoe" and "kayak" means to different areas of the continent.
It sounds like a canoe is for me, since it can haul stuff and isn't hateful to pilot alone. What should a person know when he starts shopping for a used one? To be honest they all pretty much look alike to me. Is there a go to material? This will be probably be late summer or early fall when I buy because 1) that seems like it would be a better time for lower prices than now, and 2) I have a self imposed 30 day waiting period before I do any impulse buying. It has served me well, and I recommend it.
I just got back from Quetico (Boundary waters) where we spent a week canoeing--first day we went 10 miles as the crow flies, then about 1-3 miles a day after that before coming back the same 10 miles. The 10 miles was probably about 12-15 in actual paddling, plus a lot more because we were straight into the wind the entire time and took some roundabout ways to get behind some wind cover (islands).
If I were to buy a Canoe, I'd do it from an outfitter in Ely MN, buying a 1 year old Kevlar. They're pretty hardy, very light, and they can take "big" water fairly well. An aluminum canoe is more stable, but about twice the weight--if you have to throw it on the top of your car (or portage with it) then I'd pay a LOT more for a Kevlar one. On the other hand, my family has an Aluminum Grumman (or is it an Alumacraft?) that is probably 40 years old and identical to the new ones. So there is something to be said for that.
I don't know anything about the wood, fiberglass, or plastic ones.
In my experience the downside to canoeing is that on windy days the sides of the canoe will catch the wind pretty hard. My experience was with a 17' canoe as a 15 year old, though, so take that with a grain of salt.
Aluminum is heavy and pretty much indestructible.
'Glass is a lot like Kevlar but cheaper and easier to crack. The strength will depend on the thickness, which of course will also affect the weight. A lot of glass/kevlar canoes will have a wood frame, IIRC. My lovely Chestnut is a cedar frame with canvas over top. Not ideal for a lot of uses, but it's a thing of beauty.
Picking up an ex-rental from an outfitter is definitely the best plan. You could probably even rent a boat from them first and apply the rental cost to the price of the boat.
If you want to learn how to paddle your canoe best, pick up a copy of Path of the Paddle.
Amazon
FWIW, we talked to the outfitter about the canoes. He said that he gets the Kevlar canoes at $1800, half of retail. He'll sell them after a year at that same price, after 2 years at $1,500, and after three years at about $1,200. At 3 years, he said they need to be refinished pretty good and even 2 years is pushing it.
The aluminum ones he gets at about $900 and sells at 5 years for $600.
He's starting to get into Carbon fiber, but they're too expensive and he's running into the issue that they're not really much of an improvement over Kevlar. Other than being stronger, they're not much lighter because you get to a point where it is too light pretty quickly. And you don't really need it to be stronger anyways.
We looked at canoes for a short time before buying our little sailboat. We rented a cheap plastic one at a state park and were exactly 20' from the bank when my wife decided most emphatically that canoeing was NOT going to be for her.
FWIW, a lot of the popular canoe brands have sailing add-on kits available with varying degrees of actual usability.
I own a Hobie mirage 14' kayak and love it. The Hobie mirage drive system uses pedal operated fins that propel the kayak-- leaving your hands free to fish / take pictures, or drink a beer. This thing absolutely hauls butt in the water, and is stable enough that I've taken it offshore in the ocean. (although coming in through rough surf can get interesting!) It's about 80lbs, and easy to put upright if you flip. They are a bit pricey, but you can cover a ton of distance in one. It has space for a cooler, a couple of rod holders and a few storage bins. Nothing as big as a canoe, but much, much faster and more nimble.
those mirage drives are freakin' cool.
I have a sea Kayak I bought really cheap, they are plastic, they don't glide like the fiberglass, but it makes for a great work out, easy to store, and transport. I could fit a cooler, but not much else and certainty not another human. For those who canoe, I assume you have to trailer it because they are fairly heavy to move by yourself. What happen to row boats, are they too 18th century?
Canoes go on the roof. Here's the guru, Bill Mason, showing how.
I once carried three 18' Current Design sea kayaks on a Golf.
More seriously, if you can portage a canoe you can get it on the roof of a vehicle. And my dad actually has a rowboat at the cottage that he loves. If it seems like there are a lot of non-motorized water toys in my life, well, guilty.
An Adirondack Guide Boat is the answer.
There is canoe rental on the local lake. I talked to the wife and she is game to give it a try. So we are to do that a few times and see if it sticks. I'm looking forward to it.
Those $250 10 foot or slightly longer plastic Kayaks are a blast. I have 4 of them. Just finished loading my four plus a friends in the back of my F350. 4 fit great, 5 is real tight. The wife, my two daughters and two friends are heading to kayak out in Plymouth harbor in the morning. Looks like I'll be working out of the wife's Range Rover tomorrow. Last year the whole extended family (25 people of so) floated down the Saco River in New Hampshire for a couple of days. We had kayaks, canoes, floats, and a rubber raft for the coolers and camping gear. Best, cheapest family weekend getaway ever.
I just picked up all the Okoume plywood I need to build Chesapeake Light Craft's "Expedition Wherry"
I can only work on my sailboat during the day as I do not want to bother the neighbors.. but this I can build in my basement at night or when it is raining.
I love my Pungo 140. It's an "advanced recreation" kayak. Beginner friendly but very capable. I'm looking forward to my move as I will be 5 minutes from a 1,200 acre lake.
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