Has it ever done that? It's been done it many times, and it's always either working on a room (1 action to clear, 1 action to convert to vacant) or setting up a room with the necessary infrastructure to support thosei rooms (such as a larger commissary)
Lets look at this.
Week 1: Selling Point
We had four choices (Commissary, Lodging, Merchandising, or Shop) and we chose Lodging for +2 rooms.
Week 2: Building Work
This was the first week we had regular choices and we chose to improve our building. The result of this was furnishing some rooms and the option for the Thread Board System. Although the latter is unclear if that was a result of our choices or a special event stemming from Ouroboros showing up.
Week 3: Lvl1 Wand
We crafted a wand and picked up Homer; nothing else to say here.
Week 4: Building Work
This was the second time we chose to work on our building. The result of this action was upgrading the Commissary to service 8 people instead of 4. Homer made his anti-ward scroll and the Library.
Week 5: Lvl3 Trinket
We crafted a Trinket and Homer furnished a room.
Week 6: Workshop Improvements
We improved our Workshop and Homer contributed with his ever burning fire. Not sure if he did anything else. We also promised a room for Mistletoe's girlfriend
Week 7: Research (Cursed Sword)
We researched the sword and it is unclear what Homer did but the previous week suggested he would be clearing out a room for Mistletoe's girlfriend.
Week 8: Lvl2 Wand
We made a Lvl2 Wand and there is no mention of what Homer did this week.
So we really just don't have sufficient data on what Building Upgrades involves. Two points make a line not a pattern.
Incidentally only one of the girls available as customers is new. This was the first time we met Tanner. Lappin showed up in Week 6 looking for a safe place to eat because the Witches in the forest, where she is implied to live, have gotten too powerful for her to handle. Trompdoy, Eowyn, and Mistletoe are all residents. Elise the probable cat showed up last week (Week 7) and was mentioned by name although the context suggested the girl in question (Rose) didn't know she can transform into a cat. Rose incidentally while not bidding has shown up in Weeks 2, 4, 6, 7, and 8.
Honestly I suspect that once we have a room open up again Rose is going to move in given she is probably our most frequent non-resident guest.