You don't want to underestimate the importance of nostalgia in colouring your memories (even when you read what seem like facts). I used to be a student (seven years ago) and I'm still a student now, but I look back with nostalgia on things like living in a college room, or being able to go out to buy things instantly, like you say, without having to walk into town.

On the other hand, I can equally see lots of things that are much better now (I have cats, I have a car, I have my own house, I don't have a bedder that smokes in the bathroom downstairs making me wake up in the morning to the smell of stale smoke, I have money, I have a TV, I don't have that bloody bagpiper annoying me all afternoon, etc)

But the problem with nostalgia is that it mistakenly separates out the good and the bad, so you can't consider the whole situation together in one mind-breath (I find mind-breaths a useful concept, but that may just be because I have a short attention span). I think it's better to assume that the past, like the present, is full of good and bad things, and that in principle, any two times or periods of time are inherently equal in terms of happiness.

I also think that freedom is a hugely over-rated concept. As you rightly argue, you have simultaneously gained and lost freedoms over small things. I don't think that it is helpful to view these as "freedoms" in any meaningful sense: you could just as well consider them as material gains and losses - lost time, gained a car. I think that gives you a better basis on which to evaluate whether you've made improvements or not.