dos, a more revealing amp will improve everything on your front end, be it either the tt or cd. imo, a component that can do everything 100% right doesnt exist, you can buy something that has a superb midrange, excellent highs, great midbass but the lowend might be soft and slightly mushy, or buy something with superb deep, fast and controlled bass, excellent mid and mid bass, but the top a bit laid back, lacking air and a slight bit of detail. doesnt mean that the components are crap, far from it, but you cant have everything 100%, thats where system synergy comes in, you need components to work with each other.
if you want something to match your rega in sound stakes, then demo some players, the older meridian gear has that certain analogue quality (imo) that some cd players lack. looking at your systems speakers and front end, then i'd be inclined to go for these:-
icon audio stereo 40i integrated
meridian 206b cd player
the meridian will give that sound your looking for to easily match if not better your rega deck, and the amp will work wonders with your speakers, put as a whole as a system it will sound far superior than the sum of its parts will cost and you will have all the detail, mid range clarity and a nice, tuneful bass one could ever want.
flog you amp, dac and cd player and take a punt, i guarantee you will love it!
edited to add, just thought if you do change your amp, you'll need a phonostage, the cambidge audio 640p spannered along side will complete your set up, or alternatively, at around £160 s/h, a trichord dino will be superb!