So I need new steering cables for my V-Drive and Im not sure what route to take.. Do I need to pull the cables, measure them, and order new ones or should I be looking into a rack and pinnion style conversion? Iv heard its possible and fairly simple to change over to the rack and pinnion style but I have no experience with ANY steering setups. Any ideas?
It really depends on what condition the rest of the system is in, you can spend some huge coin getting the rest of the system "up to snuff".
As for the rack, you need to buy a lot of parts not including the Rack-It system. Potentially costing more than getting the tiller cable system dialed in...
The list could include; tiller arm, steering wheel hub (depends on what you have now), steering cable end tube, tube mount and all the necessary hardware to bolt it all up. Really not a small job.

The things to check out on your current system include; pulley condition (check for wear and cracks), the springs and connection hardware, the chain and sprockets for wear, rust and cracks and also the rudder itself. Less of a job than replacing, but more tedious IMHO.

I do agree with Wayne on being "good enough", they work killer with little to no slop if done correctly, see if you can find a vee drive guy to have a look see at your current configuration, they will see more problems in five minutes than someone inexperienced could find in two days.

Good luck and don't skimp here...

GT