I looked through the entire script for mentions of buying Sylvia to double check, it's possible I missed something, but the only way I see that you could get a "I need to buy sylvia" message is after the kidnapping event, or if Felicity and Emma's level is 35. Can you please confirm which is the case? If you were getting the message from Felicity and Emma's event, and Lin was below level 25, I can see how you ran into the issue you did.
Anything you buy on the computer can be received through the "Check for mail" button at the front door. This is also true for the elves.
I'm a bit lost at the grind part. Are you saying that passively collecting bar money and watering crops is grinding? Most of the money you earn in Harem Hotel is passive income, completely hands off, except for farming, which grow exceedingly fast. All of this is designed so you can focus on the actual gameplay and mainly story.
You can do deliveries at Bernie's once a day, tend to your crops once a day, and... well that's kind of it in terms of active income. You don't have to farm if it isn't engaging to you. These things are probably 5 mouse clicks each, takes less than 1 minute to do.
Thanks for the insight into your gameplay, it's very valuable to me. I don't want there to be any big speed bumps getting in the way of the player's enjoyment. You mentioned that you were earning about $1k per week, and only able to afford Ann, who costs $2k, in 4 weeks. This tells me something (which could be wrong, but it's what I as a dev am hearing). You are spending money and not saving, possibly buying outfits at any chance and before vital upgrades to the hotel. Being this late into the game and being close to $0 is unusual from the feedback I've gotten. You could have afforded her in two weeks but you spent half of your income on other things in that month instead of saving it for Ann. (If I understand correctly, you bought sylvia, was set to $25, then had to earn $2k). The proper gameplay loop is that there should be something that you're trying to unlock at any point, buying it within reasonable time, and chasing the next thing.
I can certainly consider adjusting some prices, but it is extremely rare for me to hear of anyone having money issues in HH. Quite the opposite actually, most desire more things to spend their money on. This is primarily a story game though, think of it more as a book. Speedrunning a story is just skipping to the final page and closing the book haha. If you just want all the scenes unlocked, you can do that too. There are cheat codes available for that. But the gameplay should be enjoyable too!
This might be a good time to mention some plans I have. I'd like your thoughts.
Side Characters visiting the hotel is becoming more of a developed mechanic over time. Right now they currently just visit the hot springs, and you can have sex with most of them. But it could be deeper. You could purchase upgrades such as a professional coffee machine, hotel breakfast, and other amenities. Side Characters would begin actually using the hotel, which would get you money. If a character decides to show up in the morning, they'll purchase breakfast, maybe some coffee. Or if they visit later in the day, you could spot them at the bar, or maybe they just decided to use your vending machine once or twice that week. Most of this would work behind the scenes, except for seeing them in the bar, and it would be included in your end-of-week report, so you can see exactly what each side character did that week. So after purchasing these upgrades, it would be passive income that scales based on how many Side Characters routinely visit the hotel. Earning you an extra $100 - $300 passively per week by the end of the current update.