My answer to the original poster's question is: it depends!
My (now departed) mum had a concession pass before she reached retirement age because her illness (she was bipolar) determined that she was entitled to one. She used it to make trips into town to meet with people from her support groups and did a bit of shopping while she was there. Having such a pass meant that she didn't have to rely on anyone else to get about and it thus gave her a bit more freedom and independence. Don't get me wrong, if I wasn't doing anything her preferred method was to get me to drive her to various places, but I'd have done that anyway. Either way, if I wasn't around, having a pass gave her the ability to travel without feeling that she needed to impose on anyone else. Did she use her pass for the occasional jolly? Yes, but it wasn't a frequent occurrence.
My dad, on the other hand, made far more use of his pass to make long-distance journeys, paying only the 50p booking fee that was required on Citylink/Megabus services. Would this be classed as a "sense of entitlement"? Yes, I'd probably agree that it was, but he had worked all his life and getting a bus pass is seen as a perk of reaching retirement age; you can't blame the individual for the way the system is set up.
The biggest problem is that that people see "free" as having no cost, when this is clearly not the case. When I was a kid, concessionary fares in my area were half the adult single fare - the same as I paid, but in Glasgow, my Gran paid a 10p flat fare. The concessionary fare became 10p in my area (before it became free) and there was a noticeable spike in OAP numbers on the buses.
I recall one rather cold day when I'd just missed a bus from Aberdeen back home. I was first in the queue to board the next service, but there was one woman who tried to stop me from boarding before her, citing "we're pensioners and we're entitled". She wasn't too happy when I reminded her how much my fare was compared to hers and that on that basis alone, I was more entitled than she was.
I really don't want to get into generational arguments like this, but when the poor reimbursement rates for concessionary travel mean that I, as a full-fare paying passenger, have to pay more, it's understandable that there's a bit of friction.
Do we means-test concessionary travel? Part of me says yes - this doesn't have to cost anything extra. If you're in receipt of certain benefits you're automatically entitled to free this and that anyway, so entitlement to free travel has already been assessed. At the same time, there are always going to be borderline cases where some are just above the line.
It's not an easy situation to deal with, other than ensuring that those who are less well-off aren't placed in the position where they have to be borderline cases in the first place. And that's a whole can of worms that doesn't belong in this section of the forum!