Most brushless ESCs allow you to tune the drag brake, on mine i get (i think) 0-20% in 5% intervals, experiment to get exactly what you want, bit more on windy circuits, less (or none at all) on big circuits.
Some recommend not using any drag and just using the brakes as its possible to actually have decent brakes on a brushless. As you have the programmability of the ESC. The ESCs i use have an ABS feature, so flat out down the straight and then slamming full brakes on results in no more than the attitude of the car changing, and it slowing down extremely quickly. Doing this on brushed, from what i can remember, would result in all 4 wheels locking and the car essentially being a lump of plastic and metal sliding down the track, until it hits something. Bit trickier on 2wd but still a massive improvement on just using reverse or internal friction on a brushed motor.
No idea what the performance of a checkpoint motor is, but anything of a decent quality around the 7.5t to 10.5t mark would give you *perfect* 2wd performance, depending on what the course is like, see what the other guys at the club are running too. Other benefit is that with good brushless ESC/motors is possible to overload/boost/advance the motor to get the effect of a lower turn (but with related heat issues) or to back it off to move to (effectively) a higher turn.
Might need to move to LiPo to take full advantage of brushless too, the current drains are "significant" on start up. Unless you are already LiPoed up.
Try looking for XeRun or EzRun combos on eBay for an easy and cheap intro to brushless, IIRC the EzRuns are sensorless, so a little less programmable and tweakable, the XeRuns are sensored, and give a much more controllable drive.
And 35 runs? Jeez, don't think i could handle servicing that often
Brushless tend to need a clean (blast of compressor air or electrical cleaner) and a drop of oil on the bearings every now and again. That's it.
Do some more digging, you'll find lots of others who have had the same dilemma, i don't think many who have made the move have gone back........