how long before balance becomes "second nature"

ellsworth23, have you tried using the various anti-chaff solutions and chamois creams? You can also get them in smaller portable versions to bring on rides. Just don’t get caught having to do a trailside “application.”:o

I think these products are more for long distance but I guess it is one solution. If you are wearing out your riding patches in half an hour or an hour, just do more half hour stretches. Eventually with enough half an hours your crotch fire will hold off for a while longer. As your riding technique improves you might reduce the chafing too from less falling and wobbling. As time passes and you get calloused inner thighs the chafing will seem almost gone- until you ride for heaps of hours and wear off the skin. The other thing is having nuts breaks once in a while to allow the blood to flow.

Some people have mentioned keep your weight in the seat- this is useful until you hit bumps. Offroad riding and manouvering over small obstacles often involves moving your weight from the seat into the pedals to prevent being launched off. So keep this in mind if you always use your weight in the seat if you hit a bump it could throw you.

Everyone’s learning time is different. Upgrading to a bigger wheel and doing some serious distance will come all in good time, hopefully you will know when you are ready- the skills will transfer. Just make sure you feel pretty confident at riding your current uni first.

I used to be the same way; I even still had trouble after using biking shorts and upgrading my saddle until I finally got a seat post which allowed me to adjust the saddle up or down. I found that tilting the front of the saddle up just a bit made a huge difference in my saddle comfort. I was amazed! Certainly worth a try! Since then I’ve been able to ride comfortably for long distances w/o near as much discomfort as I once had. I’ll admit that of the discomfort was just from being a beginner and having to learn to adjust. Also make sure your saddle height is just right, a few millimeters each way can make a difference; it’s worth taking the time to dial that in correctly.

Good luck and welcome to the unicyclist community!