Up to you mate, your judgement is the only thing which will determine how well you will enjoy the car. I bought a S/C VT Calais, 150,000k's for 6.5k with 6 months rego, a littlle work here and there and I'm in a much better position than with the Silvia I used to have (try find parts for an S13 which you don't have to pay an arm and leg for).
Ultimately, you'll find a car where:
1) There'll be things you just love, and be proud of to own the car
2) There'll be things you hate, and think Holden could've done without
3) Make an impact on somebody elses decision to purchase a like car, based on your experiences with it
There are some well looked after VT's, as are VS' and VR's, but there are some shithouse ones too (me personally... looking at over 10 before I mate my purchase with haste) and I feel that even though I paid more than I originally wanted, I still feel I got the better deal.
Even with new cars you might be in the **** (bugs and **** with the cars they hadn't worked out before they sold them), it's just a matter of finding somewhere to go for your problems. I personally think that you shouldn't go for a brand spanker, and are much better off getting a tried and true car, mainly because people (like in this forum) are messing about with, and fixing them. So you don't have far to look for help.
Either way you look mate, just need to decide how you want to spend your money before hand, what exactly you want out of a car (I wanted space and power, something you can't get out of a 4, but not too much power... cause sometimes I remember just how many ####S there are on the road, who want to race and call you out for it, at least a VT is so common that most people don't look twice).
Base your decision on that, not on one person's opinion on the car (I personally had driven over 10 **** VT's before I made my purchase... and looked at soooooooooo many **** VR's and VS'.... too **** to even think of driving). My friend have all had the same ups and downs, just don't rush into it.
One last thing... How can something not "feel" like a Holden... if it's got the badge it should. Aside from that, if we were still driving HQ Kingswoods, Premiers and Toranas, I think we'd all be in a spot of bad luck (old tech like no power steering, drum brakes and the like... just saying).