Hey i'll throw my experience in the mix since I was in your shoes not so long ago. I'm probably one of the younger lads in the forum here (in my early rocking 30's).
I to tried to go the used way and 2.5 years in the hunt I never found a model that ticked all 3 boxes:
1. was price relevant
2. fit my taste
3. had all the upgrades done
I ended up never having all 3 box tickets. Either the car was all upgraded, fitted my taste but was priced very similar to a new car. Either that or it was designed by Liberace/Mr T. Sometimes the car needed so much work that it ended almost on par with a new car. I should mention that a handful of cars did meet the mark but the owners ended up withdrawing their sales offer due to sentimental attachment ...
I once had 3 refusal in one week - didn't get blue balled that much since prom.
Now my situation is different because i live in a remote country and import + duties have an impact on the bottom line so does not paying UK VAT. I therefor pulled the trigger on a new one this summer and (un)fortunately the Brexit has gone my way to make the GBP lower when buying the car.
The risk of earlier models is a roulette for the non-initiated ( I do not have the knowledge nor the space to fix the car at home) that drove me away.
I hope this gives you another perspective on the whole situation. Good luck on your hunt.