I have only ridden a 16" and 20", but I want to do some long distance unicycling. Would it be a bad idea to go straight to 36"?
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Iām in the same boat except Iāve only ever ridden a 20". I am buying a KH36er in a couple weeks to train and eventually tour parts of Europe.
If you donāt get another reply, Iāll report back and let ya know haha
But in all honesty, from what Iāve read/seen online, it seems different but the learning curve canāt be too bad - right? 
Itās certainly possible, but the learning curve will be steep.
After 35-ish years of almost exclusively riding a 20er I bought a 26" fatty (thatās about the same diameter than a 29x2"). It was a big step but I got accustomed to that within a couple weeks. The step from a 29er to a 36er was at least as big as going from 20" to 29".
You can read about my 36er experience here, if you want.
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36er is all I ride I learned on my 36er after not riding anything for 23 years.
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A couple pictures are worth a thousand words 
(Those two pictures were taken months apart, believe it or not! The pic with all of them level was taken today.)
The silver uni is a 20", the yellow/orange one is the 16"ā¦ You can see how they compare to the 36er!
For a further visual, the top of the 16" wheel reaches to about the upper-middle part of my shin. The top of the 20" wheel is about level with my knee. Meanwhile, I canāt quite fit the 36" wheel between my legs! Wearing a pair of thick-soled boots though I think I can barely stand above it. The 36er is definitely a beastā¦
I learned to ride uni on a 26" unicycle, but the jump for me still took some getting used to. The jump from a 20" uni would obviously be greater, though with some effort I think youād be able to ride a 36 just fine 
Just know itāll feel very different from what youāre used to, and itāll take a couple weeks/months to really get accustomed to it (at least from my experience)
EDIT: My particular 36er is a Nimbus Oracle, which is a more traditionally shaped uni frame. However, if inseam height is a concern, the Nimbus Nightfox should accomodate that. As an alternative to riding a 36er if cost is an issue, riding a 26"/29" uni with short cranks can be a good option. It wonāt quite have the same speed (with the same effort) as a 36er, but it would nonetheless be a good improvement over a 20" uni for distance.
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If you want to end up with a 36", Iād go straight to the 36er. I went from a 24" to a 36" with a 50 year break between the two and had no problem. It will take some time to get used to the 36" but the basic idea of riding is the same, no matter what size.
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Depending on the distance you want to do, a 36" is super stable, rolls over stuff well, and is fast with practice.
Iāve done 100km ride on 29 and 27.5 set ups with heavy tires and short cranks and they all performed well and had the ability to be customized with different tire options, itās also much eaiser to climb offroad with those sizes.
If you want to pass bikes though and go party pace, nothing feels like a 36"
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36" was fairly easy for me to learn coming fram a 24", but just fyi you can do longer distances on a 20" with short cranks
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@SirCranky is referring to putting 75 mm cranks (and probably a more comfortable seat) on your 20" and try out a couple of 10km rides and longer. (100 km have been done). There is an ongoing discussion about this in the MicroMachines thread.
Micromachining is a fun (and cheap) challenge, but requires some advanced riding skills. (EDIT: I saw from your profile that you are young and play Uni Hockey. I think you should have what it takes to try that out.) It is way harder than just riding a 36er though. A 36er is difficult in the beginning, but once you are comfortable with it, you dont want to ride anything else. This is so smooth, fast and feels just great overall. I would highly recommend any unicyclist to just do the leap and get a 36er. I use my 29er for hills, trails and Muni, and my 36er for distance riding (including hills and trails )
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I always struggle getting on my 36". That is why I got me a 32" at the time. I really like my 29" municycle with 150mm cranks and spend many hundreds of kms on it if not more. The 32" mounts just as easily and is just as agile.
I can imagine that once ur coming from a 20 or 24" wheel, it will be quite a step up to the 36" which will feel scary at first and it isnāt as agile as the smaller wheels.
Then again, you can never have enough unicycles and should have at least 1 uni for each wheel size. I have about 11 unicycles + a 28" Ultimate Wheel.
Iāll have to print and frame this. Could be helpful in future discussions about my unicycle needsā¦
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I think it is doable if you are motivated, but it will be a challenge (which can be a good thing).
In my case, I initially learned to unicycle on a 24" and then got a 26" muni and learned some basics: I could usually freemount and ride 20+ minutes until various body parts ached a bit.
The jump to the 36" was big and almost scary (but in a good way). It took me a few days before I could freemount, but worked out well. (At first I could only manage a jump mount.) But I also took the plunge and skipped the 29 and went direct to the 36 (although from a 26" and Iām 6ā1/185cm, and 36 is more difficult if youāre shorter).
I would say prerequisite is free mounting the 20" and riding down the street. If you canāt do that, then the 36" will be pretty daunting.
Although, keep in mind that it is way easier to learn on a smaller wheel (less height to go up and less to fall, so a big psychological factor). But if you are motivated and would like a challenge, then go for it.
I suppose everyone on here who knows how to ride a unicycle, has already proven that they like challenges. Unicycling comes with a steep learning curve. It took me three weeks of practising 2 hours each evening before I could ride 100 metres and then a week to learn to free-mount.
Two weeks ago I bought a long-board, which only took a few hours to learn. Naturally I donāt do tricks but the initial balancing and getting some speed in wasnāt very hard. It does have 4 wheels which helps with the balance.
Learning to ride a 36" can easily be done within a week. Just be persistent. If there is something you want badly enough, it will work out.
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29er is wheel of choice for me , iāve been on many long rides with my trusty UDC trainer and my nimbus road uni. I guess it depends on the he terrain you intend to ride on. Both Ed prat and Becky chose a 27.5 for their latest adventures. I personally am good on my 32 for a larger wheel but I have yet to take it on a really long ride. Good luck 36 seems to be the choice for most distance riders
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OP - nah it wonāt be a problem. Each wheel size is just its own thing to figure out. You learned to ride a unicycle, so you already did the hard part. I recommend the standing jump mount with pedals parallel to the ground. The big wheel requires a lot of torque to start moving compared to what youāre used to. That will give you some forward momentum and itās much easier once youāre moving a bit. Practice jumping off the front and back in some grass too. The height might feel intimidating at first and that will build confidence. Recommend 150mm cranks minimum length to learn.
Yeah, a 36er is exactly the same as any other unicycle, but different
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20" to 36" ā sure itās doable as others have mentioned. A 36" is such a nice relaxed ride when you get a used to it. There is something special about sitting high up and cruising along. Reasonable speeds without much effort. I personally belive a smaller wheel is more fun to ride but I also seldom ride more than 15km.
So why is it that the 36 is so much more sluggish to take off with than the 32". To me the 32 inch behaves like a 29". I ride a muni 29, but the 32 has a road tire. I believe even the same threads on the tire as the 36. The difference in size isnāt that big, but it feels very different.
I donāt think you need to practice jumping off the front. If you UPD you will most of the time step/jump off the front anyways, as long as you donāt go too fast. Otherwise, just leaning back and stepping off is much easier to do on bigger wheels.
As for riding in the grass, sure it is softer to land on, but it gives a lot of friction to get the 36 rolling.
When I will take the 36 for a spin next time, I will just hold on to my car or a lamp post to just get the feel of the wheel first and then try a free mount, coz generally on rides, there are neither lampposts or my car to hold on to. Or ā¦ you can carry a broom along with you to hold on to when mounting 
(not serious)
The difference in both gain ratio (pedal resistance) and circumference (wheel weight) should scale linearily with wheel diameter (you already told us you only ride 150 mm cranks). So the difference from a 29" to a 32" should feel equal to going from a 32" to a hypothetrical 35". So part of the answer lays there (your 32" is closer to your 29er).
Also, I am guessing your 29" is actually closer to 30" unless you have a rather slim tyre (like I do). That would give a difference of 2" and 4" respectively, implying twice the relative difference in both wheel weight and pedal resistance.
Then you have other āreal worldā factors that will make the 36er even more heavy and sluggish than my linear approximation.
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But you can. And you can use it when you have to stop and donāt feel like dismounting. In my case it wasnāt a broom but the stick of a garden tool that I bought while out on the 36er.