@seabisquit - I totally feel for you. I remember that it took me forever to feel "ready" to join the local beer-can race, and those races are like what you describe as a the 't-shirt' division, only more so
I understand that some people enjoy making things a close contest by racing class-legal and measured boats so that everyone competes on the same platform.
The downside is, it represents a bit of a barrier to entry and I sometimes wish that fleets and regattas were organized in ways that makes it easier for people like you to experience them (and get "hooked") so that all the rigamarole is more easy to justify. Cutting a newcomer some slack on things like paperwork in this situation isn't likely to give them an unfair advantage - unless they are experienced sailors in another class already, they are unlikely to sail competitive.
My personal thinking is that organizers are always better off giving priority to growing the field over making it a more pure experience. (This may be different in larger classes, but should be a no-brainer in fleets and classes that are still fighting to meet the minimum numbers).
Putting on sail numbers takes half an hour at most, depending on what sources you have, getting them may take a bit more, but that shouldn't hold you back.
Good luck and hope you find your own way to make the transition from wanting to participate to being there. Wish I could join you!