Congrats on keeping the season filled.
I think it's much easier / much harder regionally to schedule a season at a time. You have the benefit that most regional theaters do do their schedule by the season, so you can start a year in advance. On the flip side, there maybe less readings, workshops, short term work to be had to fill in said gigs.
In NYC, I have now stopped trying to fill anything in advance, and to be honest, to book ANYTHING but the next gig. Too often, I will get attached to a gig, start turning down and work, only to have that gig change dates, move or get canceled. I am basically looking just for the "next job" or the "the next job + one". But on the flip side, being in NYC, I can usually bank on there being a a workshop, reading, sub work or something to fill the gap. OR, given the fact I tend to work 16 months at stretch without a real break, cherish the down time. I just turned down a gig that fight perfectly in my six week gap between two musicals - because I know I will need the time off for myself (ironically, once i turned it down, musical number 2 announced a choreography workshop in that gap . . . so i filled two weeks of six . . . )
I have put together a small clique of stage managers I trust and adore . . . when I am facing a period of unemployment, I let them know - or send it out into the universe on Facebook (Beware social media, you don't want to look like you are unemployed a lot). I am also VERY good at sending jobs TO this group as well - if a gig comes my way I can't do, I make sure this group knows about it - or specific people in this group. I have been very good at sending jobs to these people - so everyone is knows I am just looking for me, I am looking for the whole group.
I am also at a point where I want to be careful about making my schedule too public, except for perhaps those "high profile jobs". Case in point, I recently finished a high profile gig. When I got that offer, if people knew my schedule, they would know I was unavailable, but when I got the offer for the show, i was able to work an out for the current show I was working on - which ended up being a win/win for me (I got continued employment and was able to take a really cool show). You get to a point where you and only you know about the parameters of what your schedule can handle, and you want to be able to discuss with people the options (like overlapping prep week with closing week of another show - able to do a workshop, by subbing out two days on Show A).
But I will for sure reach out to companies I have had a successful run with and say things . . . like I am currently work on Show A, and I am free May and June and I am looking for work. Or, just take the opportunity to network.
I think this is one of those things, wait for everyone's answers and see what fits in with your marketing/business model - take the ideas that seem right, toss out the ideas which may do more harm then good.
