Modern Buddy

Has anyone else had this happen?
I had a flat but when I took the wheel off, separated the rim, removed and patched the tube, put all back together...inflated...AND TORE A HOLE IN THE TUBE BY PINCHING IT BETWEEN THE RIM HALVES!

and not just once...I have one spare tube with two 1/4" holes on the inside right where the rim meets and now the one one the scoot (rear) is flat (again, after repairing the original flat) and I KNOW I MADE SURE IT WASN'T PINCHED.

WHAT THE !@#$ AM I DOING WRONG OR MISSING?
i think these are the original tubes from 2012 on right now, front hasn't shown any problems.

Your avatar picture is perfect for this post.

you should try putting just a little air in the tube during assembly, so it can't sneak between the rim halves quite so easily. I hate split rims myself, I'd recommend the tubeless rim upgrade if you can swing it.

I thought i did have 'a bit of air' in...buuuut nooo, opposite the stem got pinched.
need to look into split replacement.

Dust the tube with talcum powder. Makes it less sticky can help prevent it from binding to the rim and tire during assembly. My old Honda CB was tubed. No split rims, but pinching with the tire iron was always a PITA.

discovered that my (second) patch (there was already a patch, ran over a nail) didn't hold, had to peel it off and redo the fix.

so...
1) had flat from nail
a) took wheel apart to repaired flat
b) reassembled wheel
2) new flat from pinching tube during reassembly 1b)
a) took wheel apart to repaired flat
b) reassembled wheel
3) repaired tire/tube goes flat again
a) WTF!?!?!?
b) post WTF!?!? on modern buddy
c) gleam answers of hivemind
4) HAVE AH-HA! moment
a) took wheel apart to repaired flat
a.a) discovered patched fail on pinch hole from 3) remove/rerepair
b) reassembled wheel
5) inflate to stated pressure for rear (35 psi) seems too much, but that's what the SOM says as well as the tire itself...so OK
a) so far, so good

After patching/replacing, do you have a recommendation? I picked up a nail and need to patch/replace but haven't done it before. This the Stella Auto 125. I was curious if I should try to repair or replace and what advice you have for someone with limited experience and tools.

There’s some good advice already in this thread. Replace the damaged tube with a new one. The only tool needed is a 13mm socket wrench.

One thing - assemble the new tube, rim and tire, fill the tube with some air, then loosen the nuts and use an old credit card to push between the rims, making sure the inner tube is not being pinched.

I’ve been riding on tubeless rims for a year or so now and recommend them.