one big appeal of STS back then was the transparency of DC's work and the frequent updates. i came to STS after playing witch trainer and princess trainer and while i still think those games had better art, the thing with akabur games is that he works slow and back then you had no idea when something new would release. in the early days of STS you knew that DC would stream everyday and every 2-3 months there would be an update. obviously things change, the tracker is completly pointless, DC still streams most of the time when he's not sick but he's been doodling on the same backgrounds for weeks and he uses half of the stream time to joke around with his team, it doesn't really feel like he's still focused on the job.
thinking about it those akabur games also have better writing which is funny because STS has a dedicated writer and akabur does everything himself, as time goes on i more and more appreciate this guy because at least he finishes his games. STS will never be finished, i'm sorry but you know it's true. i can't even imagine the headache that implementing the dating system for all the characters will be and how many years it will take.
what summertime saga still has going for it is the chill atmosphere of a summer vacation, at least back then it was kinda cool and reminded me of a lot of old newgrounds porn games but honestly there have been lots of games especially japanese ones who are doing the whole "summer vacation" vibe much better. the main story with it's sex trafficking themes and the serious tone ruined a lot of that for me, so did the meme characters (rumps, fatther keeves, gordon ramsay and so on
edit: also back then the game showed a lot of promise with it's sandbox elements like the telescope, the strip poker, the various jobs you could take and so on. i was really hoping DC would expand on those features but the strip poker thing will probably be outright abandoned