if you're interested in the strength near the top, then i don't see why it wouldn't work. if you must core horizontally, then you've got to avoid a lot more rebar and you would need to take core along the length of the column. you should absolutely discuss it with the structural engineer. i've had structural engineers specifically tell me not to drill due to the risk of cutting rebar (we didn't have access to top or we would've cored there). as far as getting the core, it's easy enough to snap off the core after overcoring as previously described. if the structural is fine with having cores only at the top, that's what i'd shoot for.
if you're possibly looking for voids, try sonic testing since it's non destructive. in my opinion, windsor probe is pointless for checking either strength or voids in a column. at best, windsor probe is only suitable for slab areas where you have lots of probe tests and then it should be correlated back to actual field core compressive strength tests. after the correlation, then you might have an idea of where bad concrete might exist within the slab area. windsor probe appears too hoaky to actually evaluate strength...i think it should remain as an index test only. that's my opinion for what it's worth...and i believe aci has similar opinions on the matter even though i do not know where to find the reference.