Interesting responses re effects of taking ed meds young. op's lifestyle resonates and we're the same age. I started punting at 18 too, at Sandys Superstars in the nw, work out 5 times a week, and been using viagra since a teenager (not issue getting boners without, but love the increased control) as it was useful when young and partying. I don't know what will come down the line, but also of the mindset I'll deal with that day if it comes.
Where we differ significantly is that punting has never never been my only avenue. I imagine if it was I'd feel fed up. For as long as I've been sexually active, I've punted, but always had something going on with a girl outside of it whilst never being in a relationship. I think that's why I've never found the lifestyle empty. Until my late 20's was dating at least weekly, with various flings upto about 3 months at best through the honeymoon dating period I think it's called, then just rinse and repeat.
About 5 years ago discovered sa and gradually took the place of dating, since the stunners which were more occasional and took more graft in the dating scene, come in abundance there and when one finished you've got a new one the following week. I've never found much difference between the fulfilment of dating for sex and arrangements as the dynamic with the girl only seems different when I think that's she's getting money, but all other interactions are the same.
From your post, i'm not sure what you're looking for, just general discussion, looking for bareback, whether dating just for sex is worth it (you wrote:
'dating arguably is the most fulfilling option but no man has unlimited choice of women when it comes to dating', so not sure you have any interest in a relationship) or a sex life that's more fulfilling and think if they're not paid you'd get that.
I am glad I spent so much time in civvie dating when I did, as that's possibly why I now enjoy paid sex more, knowing how I can do without monetary involvement and the alleviated hassle.
Personally think you've gotta mix it up, I'd go for seeking first, and some dates, see if you feel any more fulfilment. I just find dating for sex a long winded route of getting from A to B, but do feel it should be explored (or should of by now in your case) for your own self-esteem.
Not in a position to comment on relationships, but I've always been of the mindset I'll miss out on too much now to do it, but do intend to do it some day if I've had my fill.
In short if you're not feeling wha you've been doing, seems pretty straightforward, mix it up and try something new. Good luck