You didn't say which PB in your list, but if you are writing about your 68K PBs, I have found that the commonest reason for AppleTalk/filesharing to play FBs is that the driver for an add-on NIC has gone missing because of a configuration change. No such problem occurs in OS X, but having set up my OS X Macs I rarely play about with their hardware. No such continuity exists in my G2/G3 and 68Ks however, and those are the machines in which AppleTalk spends its time reverting to printer port. These same Macs are also likely to have a faster add-on NIC atttached to the LAN than the on-board (if any) ethernet. System updates/upgrades usually have the same effect. Perhaps Installers turn AppleTalk off as a matter of course?
I also find the message 'File sharing could not be enabled' amongst the most frustrating because it contains no clue as to why file sharing could not ... &c. It usually needs that the whole set of Sharing setup, AppleTalk, TCP/IP, Users and Groups and so on be interrogated before the missing component is identified and fixed. And a missing/invisible/disabled NIC driver is the commonest cause.