When does analog compete with digital?

Disagree with Ptmconsulting about 'resonable' digital. Mostly it goes to what sound one desires. Digital has it's own flaws that no $500 or $1,000 is going to come near fixing if that stuff bothers you. if the digital sonic flaws don't bother, then it doesn't. Same for analog. A cheap TT and cart with a cheap phono, say $500. IS going to sound JUST AS GOOD (with different flaws) as that $500 digital front end. They will have different sounds, different problems with the sound, but, IMO, will really be just as good as each other.
I think the issue is: What is your preferred poison?

Bad idea trying to equate one with the other. They are inherently different Better to shoot for a single particular sound you like and tune each t that separately over time until achieved. For most, if done right, it does not have to cost a fortune.

Try not to worry about such things. Establish a realistic budget for analogue. Investigate, read reviews and search forums on personal opinions and advice. BUT! be very careful entrusting completely in what others from so called experts and those who are not may say. Gather a list of products that fit inside your budget. Study each and try to weed out the chaff from the wheat so to speak. Then you will be able to make better buying decisions. Once you then buy and carefully set up the analogue products you need, JUST ENJOY!

In time as your future tastes and budget evolve you can as per this hobby swap out other gear if you wish.

You can get great analogue playback if you are wise with buying for even under $1,000 total purchase, new or used turntable, cartridge and phono preamp. Even at this it may provide you enjoyable analogue playback that could have your CD player collecting some dust. That said I learned a few years ago to move away from being anti-digital. I got tired of the crap many say about it on audio forums. Even though most of the time my analogue records sound better or best to me I have a nice and still very modest digital setup, basically now a Oppo BDP-83 and have enjoyed playing well produced CD's too. It is just that too many CD's made over the last 10+ years suck in terms of mastering and production quality. But don't think every vinyl record you buy was well mastered and produced either, some SUCK BIG TIME TOO!

For some, including myself, your question is backward.
Knowing your Naim and speakers, only knowing your table/cartridge by hearsay, I would have to think your analog better already. Perhaps a different cartridge, not necessarily more expensive, would do the trick.
Knowing your gear/speakers, for as nice as it is for the money, I can think of many tables that I do know that better that in a heartbeat. For my tastes, anyway. For example, a RegaP3 with a highout Dynavector($400) will blow away your cd player....and I've fallen in love with Naim cd players...:)

.... that their analog front end can compete with their digital?

Never

Digital is superior for 1 reason:
- Remote