Nice job getting out there!
I've a flat tire to fix and my tires are set up tubeless, so I've been madly procrastinating.
Do it... the forecast here is beautiful for the week. That, plus daylight savings giving us later sunlight = opportunity for riding in the evening in the light!
Setting up tubeless is a messy pain. Is this your first time, or do you generally ride tubeless? So far I don't ride agressivly enough to warrant it. I can run 22PSI with no pinch flats (so far... touch wood!)