I've got to play with the X5000 quite a bit and its a nice machine. I would recommend you get a copy of 4.1 for classic and use it on a PC under WinUAE for a bit and see how you like it. If you do it runs much better on the real thing, but it will give you a base to decide. For me I prefer MorphOS and Linux on my G5 machine and 3.9/4.1 on my 4000T.
An added bonus is the RAM restriction with BigRAM+ and ZorRAM is being lifted in the next release due any time. This will allow the BPPC and CSPPC versions to address more than just the RAM on the CPU cards. It will also do this for the WinUAE installs as a bonus.