I prefer no base cup hole. I find it makes the ken feel kinda thin/hollow when playing. You just need a good natty with some grip!
I definitely might try drilling my basecup. My 1st was a super slick Walmart dama and 2nd was a catchy Air. Then I got a Rasta from Sweets which I put a LOT of hours into. Well the cups have slid down amazingly far on the spike, which is great for lunar balance but it really hurt me when I recently got a new dama and can barely stick one at all. I still haven't gotten my lunar flips back so I am tempted to just drill it.
Hmm.... I would almost suggest to not drill a base hole so you can really hone in on those lunars and lunar flips! But, at the same time.... if your current dama has horrible lune balance.... Eh
In my experience of no hole vs hole vs self drilled.... If a Ken is already pretty well balanced, a base hole can make it feel beyond honed. Loons will just slap and stay. (See the current Krom pro models) If the Ken isn't well balanced, or is poorly made, the hole won't really make enough difference. You are still gonna have to chase / fight for it. (See Amazon/ Duncan) If it doesn't have a hole, Idk if I'd drill one. I've tried and I honestly didnt feel a huge difference. Plus it's a sketchy process with the right tools. (I've drilled a Kaizen slim and a random Sweets Prime) Depending on what you are playing currently id say either A. Just keep practicing and grinding those basics. Or B. Buy a slightly higher quality Dama (if you are currently jamming something cheap like a Wal-Mart/ toys r us Dama.. Maybe try a Prime from Sweets for $15 at Target). Just my 2 cents though -edit- if that Sweets Rasta is really worn down.... Consider snagging a fresh set up.