For casual weekend riding and commuting, tubeless is honestly a nice-to-have rather than a need-to-have. The main real-world benefit you'd notice is fewer flats - especially from small punctures that a tube would struggle with. You get that lower rolling resistance thing too, but at casual speeds it's pretty minimal. The biggest factor though is peace of mind; you can run lower tire pressures without pinch-flat risk, which actually makes the ride a bit smoother on rough pavement 🚴
Where it gets iffy for you is the conversion cost and maintenance. $200-300 plus new tires is real money, and then you need special rim tape, sealant (which needs replacing every few months), and a pump that can handle the initial bead seal. If you get a puncture on the road, you've still got to carry a plug kit and know how to use it - it's not like you just swap in a spare tube and roll. For weekend cruising, that's extra complexity you probably don't need.
My take? stick with tubes for now unless flats have been genuinely ruining your rides. If you're getting multiple pinch-flats or thorns are constantly getting you, then yeah, tubeless makes sense. But if you're just doing casual loops, save that budget for something else - better tires, a nice light, or just bank it for when you upgrade the whole bike. You won't feel like you're missing out 😊