I want to indoctrinate my friends and family...

....into motorcycles. 

The three biggest obstacles I'm facing are; they are scared of riding on the street, they don't have a license, they don't have a bike.  My plan is to get a couple small cheap bikes to let them try out for some low stakes fun, see if i cant get them to make the leap to a proper bike and a license or at the least a dirtbike. ideally i would bring these on camping trips so they can putt around the forest service roads or trails if there are any nearby. 

I think i'm more looking for a moped type thing (would prefer dirt oriented) which i don't really know squat about. The contenders must be less than 50cc (No license required) and be able to be plated in WA state (for forest service roads) Any suggestions? The first "street bike" i rode was a CT90 which would be perfect except the engine is too big.

Sorry no suggestions on a small CC dirt bike, have no experience with one.
My wife just got into motorcycling and bought a Ninja 250.
For the street obviously.
Very light, and handles well enough.
I've riden it a few times, and think it's a good starter bike.
 

The three biggest obstacles I'm facing are; they are scared of riding on the street, they don't have a license, they don't have a bike.  My plan is to get a couple small cheap bikes to let them try out for some low stakes fun, see if i cant get them to make the leap to a proper bike and a license or at the least a dirtbike. ideally i would bring these on camping trips so they can putt around the forest service roads or trails if there are any nearby. 

It is difficult to force people to do things they don't want to do, it can damage or destroy relationships.
 

A Honda Ruckus may work.
It's great to have a second (loaner) bike avaliblle, but I agree with 73z1, They have to show an intrest in riding. 
I know the feeling of being the only rider in your circle of family and freinds. I recently joined VJMC, maybe I'll get some rides in with those guys. Not sure how to tell the wife, she will think I joined a biker gang.

These are people that are interested in bikes but the barriers to entry are large. I figure if I can break down some of the largest barriers to entry they will see its worth the trouble.

For example my girlfriend loves bikes, her dad had a many bikes when she was growing up shes been around them a lot, plus shes dating me and i literally never shut up about bikes so she must be into it. haha. She likes riding on the back of motorcycles but she has never learned how to ride.  She doesn't know how to drive a standard transmission, and the idea of learning on the street freaks her out a little bit, She was all set to take a "dirt first" riding course before Covid hit and since then that idea has gotten shelved. I think if i can let her putt around on something like a Honda Z50 she will love it and then i can talk her into taking a riding class and getting a dirt bike.

Also I have some friends that used to ride street bikes and have kids now and don't want to ride on the street anymore. These guys have never ridden dirt bikes, but riding trails is much safer so i hope i can get them to transition to dirt bikes because there is no worry about getting T-boned by a drunk driver.

I also am thinking about just getting some small CC bikes (less than 150cc) and not worrying about the license thing. I have never been pulled over on a forest service road and I doubt there would be any real worry about that, plus they could feign ignorance and probably get away with it. This opens up more possibilities like CT70, CT90 and the like.

PS Ruckus is a good option - thanks

The new "Honda Trail 125" is everything you are looking for so... if you can get your hands one one.

Trail riding is a great introduction to motorcycle riding. Lot's of camaraderie, fairly safe, being in the great outdoors...
Look for a TTR125 or equivalent. Easy to ride and fairly cheap. After you are done with them you can usually sell them off for close to what you payed. 

Had a lady friend ask me about this for her son. I know knowing about them but at the price point how can you go wrong. I think they are available in 4 colors. I think they have a 125 version even cheaper

 

I hear ya on growing the pack! I have stuck with always talking to the local kids, I ALWAYS let a kid set on any bike. Most of the die hard rain or shine riders I have come across grew up on a dirt bike back on the farm/ or desert. But I don't know much, hahaha.Be well all

Any of the CT Hondas, as stated, TTR Yamahas or the ever popular Honda XR (now CRF) 100. The 100 makes all of 7 hp and is almost large enough for an adult to ride comfortably. Good onya!

Here is my own experience.  As a teen I owned snowmobiles and had ridden 4-wheelers, and was comfortable on both.  My first ride on a motorcycle was friend's KX80 in the woods behind his house.  I was totally spooked by riding on dirt.  The peaky 2-stroke would spin the tire and slide sideways as soon as the power hit, and I'd just pull the clutch and stop.  Again and again.  Eventually I just went down the driveway and out onto the road.  That was fun.  It worked great on the road.  

I recognize that riding on dirt is a great way to build skill, but it wasn't much fun for me as a beginner, and I've never had the chance to try it again.  I blame in on a lack of time spent on a BMX bike in my formative years, as I chose skateboarding instead.  

I have been looking at some of the Chinese pit bikes. they have gotten way better in recent years and a 125cc "Coolster" bike with 17" front wheel is only $1750 brand new.