The plan has always been to start LO in half-day daycare in the spring (March-ish), when he'll be around 22 months. The main reason for that is DH and I are freaked out about him catching every sickness, and we think it would be way worse if we started him this winter. (And he sucks his thumb so he will definitely get sick, I'm sure of it. But this would happen during any season, right?)
However, I wonder if it'll be easier on him emotionally if we do start him this fall, when he'll be about 16-17 months old. I've been reading that older kids have a harder time transitioning. Is this true? I feel like at 16-17 months vs 22 months, either way he may have a hard transition since he's not an infant anymore and has separation anxiety already.
Thoughts?
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Hate to break it to ya...but he will probably get a bunch of colds no matter what time of year he starts.
Although I know the first winter kids goes to daycare is usually the worst. I know its inconvenient but its actually good for their immune system.
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They get sick all year round (right now is prime time for HFM) so I wouldn't really worry about that. I think younger is probably easier but it depends on your child, of course. I'd probably just go with whatever works best for you and your husband honestly. FWIW, there was a new child who just started last week in my daughter's daycare (toddler room age 15-21 months) and he had what seemed like a really tough time transitioning (the worst I've seen). It lasted a mere week and he seems fine now. So don't worry too much, kids adapt pretty quickly.
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Kids do get sick year-round no matter what, so I'd try not to worry about that. How does he do with transitions generally? That may be a better indicator than age. We have one girl in H's room that had a very, very rough transition and is fine now, and then there are other kids who just started a week ago and never had problems.
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@avivoca: What she said. Some kids handle transitions well. Some don't. Mine doesn't and it has never mattered the age or the timing. It just always sucks. Hopefully that is not the case for you! I would just what makes the most sense for your family. Though I will say LO did get sick more over the winter.
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Transitions are kid dependent. LO1 started daycare at 2 yo and LO2 at 13 months. It took LO1 3 weeks to stop crying every day and LO2 more like a month to stop crying every day.
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My son began daycare just after he turned 2. We began half days, just in the moning. Then, he began eating his lunch there and going home for nap. Then, lastly, we did afternoon nap. Took about 2 months, I think i was harder on ME than on him.
All this to say, you don't know until you try. And even then, some kids are just always going to have a hard time, like my son.
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I agree with others who have made comments about him getting sick - its going to happen no matter what the season! Sorry - just being honest.
I would start earlier and give him a longer transition. @looch: plan sounds great - and super gradual on the LO. K has been in DC since she was 4 mos full time so we never had an issue - but it just breaks my heart when I see these kids struggling when I drop K off - I wish the parents would transition them more slowly. (Obviously I understand there may be extenuating circumstances)
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Start him earlier because if it sucks too much you can always pull him out and try again at a later date. But it will be fine!
Yeah, he will get sick a lot at first but he will be okay. 
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Thanks everyone! I am just terrified of the illnesses, especially interrupted sleep (as I am sleep-obsessed). I hope that being in DC only half-days (we will probably not do full days for a long time), he still has a chance of staying healthy.....?????
@Cherrybee: that is a great point. I can try and if it sucks, I can try again in the spring. Hmmmm....there's an idea! -
My was sick almost constantly when he started daycare in March, which was only once a week. He was 19 months at the time. Now his rate of illness has gone down, so he has breaks between colds, instead of a constant cold. He also has had two ear infections in this time. It never significantly bothered his sleep, if anything he usually slept more.
He is not excited to get to daycare when I drop him off, but is usually not upset either. I am sure he would transition faster if it were more than once a week, but that is all we need. He naps well there, but does not eat particularly well, and is always hungry afterwards.
Although I know the first winter kids goes to daycare is usually the worst. I know its inconvenient but its actually good for their immune system.
Yeah, he will get sick a lot at first but he will be okay. 
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