I tend to wash/clean/lube my bikes about every 2 to 3 weeks, depending on riding conditions. The tubeless punctures I've had haven't made that big of a mess, and it cleans up just as easily as road grime when you're washing the bike. So for me, at least, I just wash my bikes regularly and it's no big deal.

I'll check the amount of sealant once every 6 months, and top-up if necessary. Now, I'm a little bit anal retentive, so I'll remove the valve core, suction out all the sealant to see how much is in the tire, top-up, and put the sealant back in the tire. That whole process takes about 10 minutes. If I were just going to add sealant, it'd be a 5 minute job, if that.

I've got three bikes, only one of which is tubeless. As long as you don't puncture, tubed takes less time overall. My guesstimate is that if I got two flats on tubed, the total time investment would equal tubeless. Once I get above 2 flats, the time investment would shift dramatically in favor of tubeless (especially if I flatted on my Cannondale w/ Gipiemme rims . . . those things were just as much of a PIA to mount as tubeless).

Although I put more miles on my Emonda (tubeless), I commute several times a week on my Cannondale (tubed). I really want to go tubeless on my Cannondale. To me there's value in getting a flat and not having to stop -- or minimally pull over and add some air -- and still be able to get into work on time. No matter what, if I flat on my tubed Cannondale, I'm not getting in to work on time. Converting to tubeless would change that for me.