[@Hmmm]
Basically, do we all absolutely have to play the young novice setting out for adventure and growth in the magically dangerous world? Because that's kinda boring IMO, in the sense that it limits the scope of what characters the players can bring to the table. And in general I find it's just not a great idea to bet on long run development in freeform where people often drop out from one day to the next. Sad but true.

As a suggestion, why not allow older/more developed characters as guild "apprentices" simply because they had not joined actual guild operations until the start of the roleplay? They could be foreigners or soldiers or independent contractors or really anyone who didn't participate in adventuring as mandated by the guild but engaged in similar/relevant work. All it'd take to justify people wanting to join a guild over their previous line of work are incentives like better pay or support/services rendered to guildsmen.