The plan was to be on pair with the legacy version by the end of summer. I don't believe he will be able to keep that up, but I also don't think he will be far from it. Of course we don't know how the new paths will look and of course he changed the story flow as well.
The day one demo is nothing but a day one demo. It was planed as day one demo and that's why it only has day one in it. By the time it was released he had already done more. In the source files you can see several random event scenes that are not visible on day one.
I don't know what his plans are, but to me it would make a lot of sense to focus on fleshing out some repeatable content with the girls you can get the farthest with the fastest for the next release. So for instance put the photo shoot with Kira in there and let us start fucking Kira.
Put a fleshed out version of Alice's girls night out on Friday night with Kira. Alice and Kira both have reason to be not just a little drunk that night, but absolutely hammered. So it's completely believable for us to be able to do pretty much anything with either of them on Friday nights. Alice could legitimately not remember what happened or she could pretend not to. For Kira it doesn't really matter IMO, but I think it makes more sense for her to remember everything. I also think it would be interesting if there was a version where Max stays on the couch and watches TV and both Alice and Kira head to the bathroom and lez out on each other with Max obviously having an option to catch the show.
With the girls going shopping on Saturday I think it would also be nice to have a repeatable daytime scene with Kira which can escalate to pretty much anything while she's alone with Max.
Progress with Lisa and Ann are presumable going to be a slow burn so it doesn't really matter if there's much if any progress with them in the next update unless he plans on waiting for the next release until he's actually caught up with where the previous version was. I would agree that catching up by summer seems unlikely given his track record, but I'd love to be proven wrong on that.
Personally, I would also love to see a scene along this line with Ann being the one watching and Kira being the one on the couch on Wednesday and Sunday nights: