My daughter is two and a half, and I currently have her signed up to start the town preschool in the fall for two days a week. I'm hoping to also sign her up for the Waldorf-inspired waldkindergarten another two days a week. Why both? With the town preschool I have a better shot of her being able to go there, and a friend of mine can pick her up (I have a 45 minute commute to the city) when she gets out.
But I want her to have the benefits of waldkindergarten, too. I'm not 100% sure what my fall schedule will be (I'm an adjunct college instructor), and no idea about my DH either (he's been looking for a full-time teaching job).
Cost is not the worry, it's more the transportation thing. Also is it crazy to have two different kinds of schools?
I know several families that do two different preschools, mostly because with the small population around here no one school is open all the hours the people need, so they have to juggle things. For some of them, it works fine. For some it's pretty draining on the kid. I can think of one 2 year old boy that was doing 2 different preschools, and he was getting overwhelmed by the frequent shift in who was responsible for him. He now only goes to one of them (and still has a hard time some days, actually!)
The transportation issue will seem daunting--until it isn't. You'll find a schedule and routine that works. It might be a pain, but once you have it figured out it should just keep working.
The only kids I know who go to that much preschool at that age are kids with special needs. However they are going to the SAME preschool with the SAME teachers & SAME kids. At 2.5-3 going to 2 different schools with different teachers, kids & methods of learning/sets of expectations may be quite confusing.
Both of my children attended a Montessori half-day and a kindergarten half-day program and it was fine. They adjusted well and the differences in rules and routines in the different classrooms didn't phase them. They were/are fairly flexible and accommodating children (now almost adults!) though, so I was never concerned that they would have trouble. They had also been well-established in the Montessori classes for a few years by the time they started kindergarten. Perhaps they might have had a little more difficulty if they started both at the same time. I doubt it though.
As you say, the biggest issue was solving the transportation dilemma. It was a headache sorting it out at first, but after the initial work was done organizing it, I didn't really think about it again.
I have very social children and they loved being part of different social groups and expanding their network by attending 2 groups. I'll warn you that it does make life much busier, because you have double the number of invitations for playdates, birthday parties, summer picnics etc. as well as school concerts, spring fairs, classroom observations, etc.