Wizards removing the workweek daily events has actually seemed to be a boon for tournement players, as the dailies are firing again with some regularity. I have no direct concern with the dailies failing to fire as I have yet to try to play in one in the four months since buying in, but I am worried about dwindling interest in Vintage on MTGO. I don't really care what the price for Power is as I assumed I was never going to get my money back, and I was okay with that as long as I could play Vintage as frequently as I want. I still don't have troubles finding games regularly, but I have noticed reduced traffic in the tournament practice room. I hope falling prices along with the holiday Vintage tournement will inspire more people to explore vintage.
I wanted to respond to your last sentence more specifically. While "soul searching" strikes me as somewhat over dramatic for discussing something as mundane as spending money on a game, I think it is valid to ask what someone wants from their MTGO experience. If the answer is to have fun playing a digital version of a very fun game, I would still strongly recommend buying in. As I am not been playing for prizes any bugs I have encountered have been meaningless. If a user wants to play for prizes (as nominal as the are for DEs) then all the well documented shortcomings of the platform have real consequenses, and a potential user needs to question whether they can tolerate these problems or if they will outweigh the enjoyment they will get from playing the game.
Was my use of "soul searching" overly dramatic? Without a doubt it was. As you stated, I really just wanted to convey to someone who was thinking of buying in to really think about what they wanted to get out of it. Perhaps I did a poor job of clearly stating why "Vintage on MTGO is still like playing anything on MTGO, except worse". MTGO is what it is. For all of it's short comings it's still a way to play MTG and I can live with MTGO in it's current state.
A lack of traffic in the tournament practice room, dwindling interest in vintage, and daily events relegated to only the weekends that still only fire with some regularity doesn't exactly equate to a boon for tournament players. It is however a big part of the concerns I have had with buying into the format via MTGO. What I wanted was to experience the vintage format. While you could argue that I have achieved that, unfortunately for me the tournament practice room has had a noticeable drop off in activity for vintage games and it's getting increasingly difficult to find more than 1 or 2 games with a different opponent a night. Like you, I am also not a "tournament player", but I have been willing to spend tickets on the dailies in order to get exposure to the format since I have none up till this point.
With Vintage being a somewhat niche format with a small community when compared to the other main formats, MTGO should in theory should make it easier to consistently find a Vintage tournament or a pickup game. Getting to play on a regular basis at first and see the player base erode away in the month that I have been playing the format is downright depressing. That is what has been extremely disheartening for me. That is why I would not recommend someone buying in. Without VMA or some other Vintage product to push, I fear WoTC isn't going to do much else to keep the format going other than putting it on life support which they have already done. I suppose I don't exactly regret "buying in", but with the experience I've had so far and the current outlook for vintage on MTGO, it does make me wish I would have used that money towards "buying in" for RL power instead. I'd probably get to play in about as many tournaments as I do now anyways.
I have found an amazing format with an equally amazing player base. I have not had anything but enjoyable interactions with anyone that I have encountered which I definitely can't say about the other formats. Vintage is amazing and like you said, hopefully the Winter Celebration helps promote the format so others get to experience how awesome Vintage truly is.
