I played this before it got "rebooted" Is the content past the old version and how long til a final release could be expected?
Still going with "Maybe" on that question. It's quite a bit further along in some quests, but others took a completely different directional turn. You'll hit a point and it'll feel like you're playing a different game. A related game, just different. Also, if you check the current file size... yeah, it's a beast right now. My current playthrough is at just over 50 full hours. I'm using Okutno's page to money cheat my little black heart out, too. There's a lot of mini-games, and not gonna lie: some of them are good, and some of them suck. YMMV. If you're willing to take the plunge though, strap in and hang on. It's not a short ride.
Which makes your second question harder to pin down. It kind of feels like we're getting closer to an ending, and we're certainly getting little teasers of animations that might make the sequel game whenever Beggar goes on "staycation". OTOH, Beggar also introduced new mechanics recently regarding using your gang as a passive income source. It "feels" like maybe Beggar is setting up passive income, (where you don't actually have to work a job), to be YouTV in the early game and gang jobs in the late game. He pulled a lot of the YouTV content he had a few updates back, though. All the milestones are still in the game files, he just seems to be planning to rework it some. Also, the gang jobs are a tutorial right now, with no actual quests added yet. If you're die-hard "I'm not playing until it's done", you'll be waiting awhile.