I actually work for a TV company... might be able to give a little insight.
Most headends for hotels, hospitals and the like are comprised of a rack of STBs, each tuned to a specific channel. The output is modulated as an RF signal and combined with all the others, so the incoming digital signal is effectively converted to analog for redistribution on the local coax network.
So, if you're wanting to display more than 32 services, you'll need at least that many STBs at your analog headend. You'll also need to manage the infrastructure to distribute it to the six buildings, which would probably mean running underground cables underground, and if there is any sort of distance you'd need some RF amplifiers. You might be able to get around some of that using something like a slingbox over IP, but again, added cost.
Finally, there's the management aspect. What happens if a channel moves to another channel number? You'll have to retune the box. If a box goes down for any reason, you'll have to replace it as the channel will be knocked out. And one of the less fun aspects of managing a TV system is that people treat it as a utility... if it's down, expect to get a call, even at 3AM.
If I were you, I'd push your cable company to donate STBs in order to keep your relationship rosy. That way, no $3/month fee (which does seem wrong based on your agreement), and none of the buildout/management headaches.
Best of luck.
