Thanks for that link! What a beauty - I forgot she's a Rhodes design.
We owned a couple of wooden boats so I have an idea what I'd be facing. We easily spent as many hours maintaining SQUALI and ALTA as we spent sailing them and they were not large boats - 21' and 23' respectively. SQUALI was mahogany on oak frames and like LITTLE PACKET, had painted canvas decks. ALTA had a clinker hull of oak planking on oak frames, all naturally-finished. Her decks were teak. They were beautiful boats when everything was in good shape but often you just wanted to put the sandpaper down and go sailing.With regard to LITTLE PACKET, you sound interested?
And yet, the tug of uniqueness and nostalgia is still there, and these boats will not be replaceable once they are lost to neglect. I've considered going to have a look.
Regarding tillers, I spent most of my sailing years in dinghies. While Rags behaves as you describe it would be difficult to get used to a wheel. It's only a 33'er - I'd be looking to convert it to a tiller.