I have spent a significant portion of my surfski career surfing motor boat waves. There is a lake near me that is congested with fancy motorboats in the summer and I go there with the express purpose of surfing boat wakes. Holiday weekends are the best. Most days people start filming me with their cell phones and every now and then people toss me cans of beer.
There are better and worse boats to surf. Old wooden motorboats with square sterns and vertical transoms (Chris-Craft is a good example in the US) are the best. There are old fiberglass boats that have that same shape and are great to ride. More modern hulls are more fuel efficient and generate smaller wakes. Wake boats are not as good as you would think, but sometimes the pilots are happy to give a surfski a ride as they understand the thrill that we are after. Regarding size a 15 foot boat can leave an ok wake if it is loaded full of people but generally 20 ft and up are the ones that create massive wakes. As MCImes said, the best waves are created at speeds just below where the motorboat starts to plane, I would say 8-11 mph with 10 being perfect. 12 mph is a very hard wave to stay on.
If there are lots of boats cruising where you paddle then you might not need to have your own motorboat. Just ride random boats. There are 2 ways to catch wakes, one is to start behind the boat when it is slow, and paddle behind it as it builds speed. When I want to do that I hang out at narrow channel where all the boat traffic has to slow to 5mph to get through. If the people in the boat show interest in you then can chat them up and they might be happy to to drive the exact speed you want. it gives then something to look at for 10 minutes while they drink beer.
The other way to catch a boat wake is with a high speed assault. Find a boat going about the right speed and distance from you that looks like it has a good wake. You will learn to recognize what is good and what isn't. You then need to put yourself on a collision course with the motorboat. You are on a collision course if the angle between you and the motorboat is not changing. for example, if 12:00 is straight ahead imagine the motorboat is ahead and to the right at 2:00. If as you paddle towards the boat it remains at 2:00 then you will collide with it. You can adjust speed and direction to maintain collision course. Then it gets a bit psychological. If the boat thinks they will hit you, they will veer away and you will not catch it. So you have to look innocent and harmless. What I do is set myself on a collision course with a spot just behind the motorboat. I paddle at an easy pace, maybe 6 mph. I have relaxed body language. The motorboat sees that I am no threat. Then as I am getting closer to the boat, at some point I accelerate to maybe 8.5 mph and simultaneously change my coarse to be on a collision course with the middle of the boat. The motorboat is caught off guard as they had no idea a kayak could move that fast. Usually I do this late enough that the motorboat cannot react by changing course. Be careful not to aim too far forward; if you do so the boat will get spooked and turn away. Finally I sprint violently and pierce over the foaming boat wake just behind the motor. A quick turn is required as I cross the wake. The goal is to be on first wave. The subsequent waves are smaller and much harder to ride.
The best boats to ride are often wealthy retired guys. Those guys are entertained by the spectacle, and secure in their place in life so they do not feel their manliness is under attack . Younger guys, say 45 and under, often feel threatened by the presence of an athletic guy riding their wash. This is especially true if they have women on board. If I sense that the pilot of the boat does not want me there I abort the mission immediately. Not worth antagonizing anybody and not worth getting surfskis kicked off the lake. Sometimes I can see by the body language 100 yards away that they guys does not want me on his wake and will just accelerate and turn away if I get close.
There are risks to this game. I have never had a problem or even a close call, but I paddle with eyes on the back of my head and wear high visibility clothing and pfd.
Current Skis: Nelo Vanquish AIR, Epic V10g4, NK 670 double, NK exrcize, Carbonology Feather, Think Jet, Knysna Sonic X
Former Skis: Epic v10g3, Kai Waa Vega, Epic V12 g2, Epic V12 g1, Epic v10 double, Nelo 550 g2, Fenn Elite S, Custom Kayaks Synergy