Pirelli Cinturato Velo on DT Swiss R500

I have not used the tire / rim combination you specify.

The DT Swiss website has information on recommended tire pressure and dimensions that include information for a tubeless setup indicating that tubeless is manufacturer supported (with caveats) for the R 500 rim.
Tire Pressure and Dimension PDF
Rims - User Manual

3.1 FITTING THE TIRES WITHOUT A TUBE
DT Swiss recommends the use of the separately available DT Swiss Tubeless Ready Tape and DT Swiss tubeless valves. The DT Swiss Tubeless Ready Tape must be used in the width appropriate to the rim. For further information visit www.dtswiss.com.

DT Swiss offers no functional guarantee for the tubeless system since we are unable to exert any influence on the tires and sealant used.

NOTE Potential damage to the rim from unsuitable sealant fluid!
• DT Swiss recommends sealant fluid not containing materials which increase corrosion. If in doubt, you must contact the manufacturer.
• The rim base must be inspected regularly for corrosion damage. If there is visible corrosion, the rim must not be used further.
• In the case of corrosion clearly caused by the use of unsuitable sealant fluid, DT Swiss declines any liability and warranty whatsoever.

1. Make sure that DT Swiss Tubeless Ready Tape and a DT Swiss tubeless valve are mounted.
2. Put sealant fluid into the tires. Comply with the instructions of the sealant manufacturer.
3. Assemble the wheels according to the manufacturer's specifications. → We recommend using soapy water or installation fluid.
4. Pump the tires up to their maximum approved pressure. → The lower of the pressures specified for the rim (see table at start of this user manual) or tire applies.
5. Check the tire bead seat. → The tire bead must contact the rim evenly around its entire circumference. → Have the tire bead seat checked by a professional if in any doubt.
6. If necessary, reduce the tire pressure to the desired operating pressure.

I have no experience with this specific tire and rim combination, and I see that nobody has mentioned any general experience with DT Swiss rims. This answer will try to address the features of tubeless rim compatibility you identified.

Performance road tubeless tires at or under 28mm wide are run at high pressures. The higher pressures appear to reduce the margin of safety, making the rim dimensions and tolerances much more important. For example, Rene Herse cycles says that their tires (made by Panaracer) must not exceed 60 PSI when installed tubeless. The image below was taken from Zipp's tire pressure guide for its new 303S wheels, and it also recommends relatively low tire pressures, even for 25mm tires.

The tire the OP specified, the Pirelli Cinturato Velo, is a road tire. Even so, I'd expect most users to be under 60 PSI even on paved roads. Thus, I personally wouldn't worry about the relatively small hooks and the lack of shoulders beside the center well. It's worth noting that if you rarely puncture, installing the tire tubeless or with light butyl or latex tubes should give about the same rolling resistance. This particular tire is advertised as puncture resistant.

The shoulders on either side of the tubeless well should help keep the bead in place. However, they would seem to be more useful to prevent the tire bead collapsing back into the rim under lateral force. Indeed, one document by Hunt Wheels says

The H-Lock profile also secures the beads in place more firmly once seated. This is especially important when running lower pressures or for off road riding.

Thus, even if the OP is planning on some light gravel (more likely dirt roads, possibly with some loose stones), I'd still expect them to be at relatively high pressure, which should do the job of maintaining the bead's position when cornering. Thus, I wouldn't view the shoulders as critical for this use case.

I am also not sure how critical the size of the bead hooks are. This post by Slowtwitch.com is a review of an Enve tubeless tire, but it also mentions that many of the larger carbon rim manufacturers are moving to a hookless design. The article claims that the hooks are a fail-safe if the tire is too large relative to the rim, or if its bead is too stretchy. If so, I'd expect that the mere presence of hooks should be enough, unless you are planning on running very low pressures off road.

I have run Paranacer tubeless gravel tires on DT Swiss rims similar to the R500s (specifically the ones on the C1800 wheels; I'd expect the rim profile and tubeless features to be similar). I had one incident where the rim deflated unexpectedly while off-road, but I don't think I hit anything and I wasn't cornering that hard. I was running relatively low pressures (~35 PSI). However, this is one anecdote, and I'm not sure that generalizes to DT Swiss rims.