I'd agree with @audioengr and keep your transport and get a good jitter-reducing device, then get a good DAC -- there are so many more great ones out there these days than standalone players, and good digital cables are also very reasonable. Since you're an analog guy you might take a good look at some of the newer R2R NOS DACs that tend to have an innate natural and organic quality that may appeal to you. In your price range I'd look at the Metrum Onyx or one of the Schiit DACs. Best of luck.
Upgrading my Redbook after 18 years
My vinyl system is my primary source but have ventured into headphones as a second system with Redbook being the only source I use. Headphone listening is provided by a newly broken in Schitt Gumby thru a Cambridge CDX transport and I have started using the system more and more, am really impressed with the Gumby but would like to upgrade the transport and the Bell Canto CD3T has come to my attention with the bnc connection which as I understand would behoove the Gumby. I will also like to upgrade my 18 year old Wadia 8 transport and my Jadis D2 dac in my main system and was thinking maybe a single piece CD player in the range of $2,500.00 slightly used or demo. On my main system I like what I have better than the Oppo players so other suggestions will be considered. Please note SACD isn't needed and have no plans to download, stream of other sources just Redbook on both systems.