I built a hotel PMS system in 9 months without trying to sell it first to hoteliers (no industry experience, talked only to 1 hotel owner). Found out it's hard to sell it, even if almost/fully free. https://hoteliera.com/
Yes, they're cheapskates. And there's a ton of them, so initial sell is high touch. But there's been a lot of modernization among them, yet their client-facing web presence really isn't being served. So once you've got them, I'd expect to be able to hold on to them--low-touch--for a very, very long time.
Just an idea...