Cartridge and Phono advice for Classic 3

I think you may be rushing into this. $5000 is a lot of money to spend on your first phono preamp and a cart.. There are big differences sonically between various analog components. What you are doing is no different than someone asking "I'm new to high end audio. Can someone recommend the best $5000 speaker". (I use the speaker example because it sounds like you know audio, just not vinyl.).

I think you need to do some listening, or possibly get a more entry level setup so you can figure out what you like and don't like, before you make a major commitment on components. There's no shortage of good equipment out there, but that doesn't mean you will like all of it. You may want to give The Cable Company a call. They should be able to send you out a bunch of stuff to try first so you don't end up making a big mistake.

That is fair. I would like to still spend the money on a solid turntable like the Classic 3 as I have auditioned numerous tables and that one is by far the best I have heard in a price range that I am willing to spend. can you recommend any more entry level equipment that may be appropriate to try out then with that table to get a better understanding of what sound is more appealing to me?

Usually Lyra and Dynavector seems like the most popular cartridges to go with VPI, followed closely by Soundsmith.
I have not heard Soundsmith but certainly you can't go wrong with LYra or Dyna depending on your listening preference.
If you want to be a bit more adventurous and have a chance to auditon, you might consider Miyajima as well. I am using Miyajima Zero mono cartridge with VPI Classic 3 and it is a sensational pair.Big meaty sound, a little woody, excellent speed, bass and slam.
However, Miyajima's compliance is a bit on the lower side, mono cartridge is 8x10-6cm/dyne which is the highest for Miyajima and I have no problem with VPI Classic 3. I am not sure of the current US retail price but some of the line should definitely be in your budget. However, Shilabe is probably fit right in your budget but has the lowest compliance at 5 and most likely would not work well. Kansui would be a better match for sure but it may be a bit beyond your range.
Try to audition it first if you have a chance!

Suteetat have you heard Lyra and Dyna cartridges on your Classic 3?
I intend to audition both types of cartridges, but was wondering what differences you found between the two brands.

If I were you, I'd consider a high output cartridge which would eliminate the added expense of the phono pre. There are many good ones that would mate well with your arm on the Classic....