What to upgrade first?

SCMCA: I have a pair of Castle Acoustic's Isis speakers listed for sale that are well within your budget, they are very good for your source material and I feel that the reviews are fairly accurate. Review sources of the speakers are listed in the ad. I was running them in an 18 x 24 room with a musical fidelity X-A1 amplifier that is rated at 50 watts per channel. The speakers sounstage and image well when placed as close as 12" from the back wall which is a nice feature in most living room applications. They do need decent 24" sand fillable stands though that should be available for around $100.00. Other speakers that are around the top of your price range that you may want to check out are Linn Tukans (now discontinued but available on the used market), the small PSB's that DanVet mentions and Coincident Triumph Signature's that can sometimes be had for $600.00 or so. I am for upgrading the speakers first as you can see. I am familiar with your CAL player and would leave that for way last following your amplification and cabling down the line, granted that you like its sound. The CAL has a very full, balanced and musical character to it, IMO and is hard to beat without spending a lot more money. I use a CAL Icon Mark II now as a tranport but used it as a stand alone as well and am partial to CAL's sound.