I hear ya.
I sort of figured I would be going down a bit of a rabbit hole on this winter mechanic adventure.
As an experienced 56 y/o cyclist who has been doing road biking for 40+ years, I’m looking at trying tubeless as another part of my cycling resume’.
The more I can de-mystify it, the more proficient I become. I would love to put a full season on tubeless road clinchers for 2019 and sort of chronicle the results. Even if it is rejected, I believe it will not be a fail.

Riding some nice tubulars does sound fun as well. I’ve got a mini stash of some new 700x25 Conti Grand Prix 4000 tubulars just waiting to be glued onto Campy Bora Ultra tubular wheels that are new in the box.

With a full time job and numerous family responsibilities, achieving small steps towards getting one bike roadworthy gives you heightened enthusiasm that all the little bugs really can be addressed, one at a time...