#1
I was thinking of buying a Road Worn JM body that typically has a 7.25'' radius neck but instead of using one of those, just use a 9.5'' radius neck instead, would it be possible?
#3
Shouldn't be a problem at all. I'll be judging you, though.
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#4
No problems there, so long as you can adjust the bridge to the correct radius, which you normally can on a jazzmaster.
Rig Winter 2017:

Fender Jazzmaster/Yamaha SG1000
Boss TU-3, DS-2, CS-3, EHX small stone, Danelectro delay
Laney VC30-112 with G12H30 speaker, or Session Rockette 30 for smaller gigs
Elixir Nanoweb 11-49 strings, Dunlop Jazz III XL picks
Shure SM57 mic in front of the amp