I say go for it.
The first setup will be a bit of a hassle & learning curve but after that it's really not that big a deal. I recently set up a pair of A23 with Specialized Terra 2Bliss and they inflated just fine with a floor pump. Here's my hot take:
- Get tires that are rated tubeless-compatible. Regular clinchers can work fine but you might as well stack the odds in your favor.
- Unless you have stuff lying around in your parts bin, just go ahead and order the velotape 21mm conversion kit. Different valve stems are shaped a bit differently so, again, stack the odds in your favor.
- Be semi-meticulous about having a clean, dry rim before you install the velotape.
- After you've installed the velotape, but before adding sealant, install and inflate the new tires WITH A TUBE. Make sure the beads are perfectly seated on the rim, and leave them in there for a little while (>10 minutes, say). IMO this is an underrated step in the process. It really helps the tape adhere to the rim, and also helps the tire conform to the rim.