I think the issues you talk abou here are interesting. I would say that the opening the paragraph that you use to link in to these issues is something I don't personally see - my sense of my backlog which is something I'm very aware of is not something that has a connection to me feeling that games are more important to play at their time of release. I'm ok with games later and feel that they still hold their value though I concede that occasionally I want to play a game at the same time as other people to be a part of the zeitgeist and the discussions that follow soon after - the last example of that for me is Portal 2. In general though, I'm more and more ok with playing games whenever.
I think I'm ok with remakes of games making others obselete. Some things have just moved in ways that are only positive wwithout any negatives. They are other improvements that come at the cost of losing other things for value and in those cases I agree that it can be good for people to try out those things - that won't be for everybody though. There are some gems of games and types of gaemplay as well from the past that have just never been followed through on since then and where something really valuable has been lost - even more important in those cases that those things aren't lost where they're useful. It's probably most important that future game designers know about those old games so that the best tthings can find a place in new generations of games.
This reminds me that Paul Barnett (frequent Bombcast contributor) said that he was bringing up his son by starting him playing the earliest generations of games and gradually working him up through the timeline of games so that he took in all the important games of the past and games have gradually progressed - that sounds a pretty amazing way to go about things for that kid. One of the things we can lose the most by forgettting the past is how amazing what we have today currently is in many ways.
Interesting to read your thoughts - I'll be following in case I find other things interesting that you write.