I completely agree with your outlook on the last part, Destiny 1- I'm not sure if you played it or not- took the exact same path to playable as Destiny 2.
For someone like me, I have an extremely difficult time finding a game I truly enjoy playing everyday. I frequent games like Rainbow Six Siege, Realm Royale and other simple one-off games that often don't have much progression behind them.
Games that do have progression-based gameplay like The Division, WoW and other MMOs are either too much grind for me or too little of what I'm looking for. That's why Destiny is perfect for someone like me. And my boat seems to be a pretty common one, which is why I consider it to be more than just baseline playable in my case. I'm actually excited for the weekly reset again!
With all that said though, I would never encourage someone to purchase both Forsaken AND the Annual Pass at the same time, especially considering their history. I would hate to have someone try really hard to enjoy forsaken- only to feel "meh" about it by the end.
The Annual Pass is something that should only be purchased after having experienced everything that Forsaken and the base game of Destiny have to offer.
On that note though, I do agree that anyone who purchased the base game of Destiny 2 alone has every right to feel dissatisfied and distrusting about the game's future. Pre-ordering Shadowkeep is without a doubt not a good idea.
But with all that said, I do strongly feel that the Annual Pass was a purchase that was fairly priced, even if I feel that Destiny 2's economy and base gameplay was not originally worth it's 60$ pricetag.
On a side note, I am also getting my technical degree in web development at the moment- so I'll be soon to be in the same boat as you potentially. (lol)
I think that if shadowkeep is a reasonable expense for new players, then it'll resolve the sting of jumping in right now, and unfortunately I don't think that there's going to be a way to redeem the expense of this game to longtime players. I too played Destiny 1, back on PS3, then ditched it on similar mediocrity, then picked it back up on PS4 at Forsaken King, and enjoyed that for a bit but lost interest before further expansions could come out.
I think where we would definitely agree is that $30 for a progressive content offer is actually pretty legit. If they can keep providing something worth playing for $30 here and there, then right on! That I think I can convince people to come and try, and I think I would be willing to keep doing that in the long run. But the stacked $90 twice a year or so per person, gets to be a bit much given the amount of content provided. Story missions have universally fallen flat with little to no enjoyment for me, and I'd rather just not pay for them until they improve somehow if I could.
I think it's really a matter of perception. Given that there was distance and time between D2 launch and Forsaken, it doesn't feel like it from the consumer who feels like "I just paid for this! It's awful! Now you're telling me you've finished your work and you want me to pay you again!?" It feels like an unscrupulous contractor that you would rather not be working with in the future.
On a personal note, wish you the best with your Webdev degree, Frontend/Webcode is what my wife does, I do Data Arch, Art and writing and backend. It's a fast paced ever changing work environment. If you end up having a question about something sometime, you can DM me and I'll answer when I can. Do not get daunted by the interview processes, there is a definite song and dance to that. Good luck and good skill!