Sounds like this would be a great market for a company like Hipmunk, Adioso, or Square to develop an app targeted at indie hotels.
If I'm Hipmunk and I'm running into the sort of issues described in this post (people w/o computers using fax machines to manage reservations and making me look bad when I misquote a customer because of it), I build a best of breed tablet app that electronically keeps track of all the complexity the little guys use paper for. It syncs with my cloud so I always have the most current information, and it integrates with my competitors too to make sure that no hotel has any reason to keep me from having the most current information.
Then, I start a rollout program where I'll send your hotel a free tablet /w the app preinstalled in exchange for $500 worth of booking credits at your location. I target the hotels in the most popular areas that currently give me the least accurate data.
Remember that the context for many of the hoteliers you're talking about (old paper systems) is very different to the solution you're proposing (easier electronic systems and more profit).
Many of these hoteliers are running a lifestyle, not financial or business, context. Invest in new systems (and learning new systems)? Not worth the hassle. I even stayed with one hotel (7 rooms) - their problem with OTAs was being sent too many customers. They rarely wanted to be full, and they also hated 1 occupancy nights.
If I'm Hipmunk and I'm running into the sort of issues described in this post (people w/o computers using fax machines to manage reservations and making me look bad when I misquote a customer because of it), I build a best of breed tablet app that electronically keeps track of all the complexity the little guys use paper for. It syncs with my cloud so I always have the most current information, and it integrates with my competitors too to make sure that no hotel has any reason to keep me from having the most current information.
Then, I start a rollout program where I'll send your hotel a free tablet /w the app preinstalled in exchange for $500 worth of booking credits at your location. I target the hotels in the most popular areas that currently give me the least accurate data.