DS1 has been at his nursery since he February, 1 full day amd 1 morning per week. He's nearly 3.5yrs old. I chose the nursery as it was local and has a fantastic garden and consistently outstanding Ofsted inspection report. It also had a lovely feeling.
Unfortunately I ended up with DS2 (18m) at a different nursery as original childcare plans fell through and there's no baby room at DS1s nursery (relevant in a minute). This is hard in the mornings but I just about manage it.
Anyway, DS1 struggled to settle initially,he is quite a 'sensitive' child so I expected this. There was a good few weeks of tears at drop off. Eventually these stopped and he would just walk in, which was wonderful, but this only lasted a few weeks before we were back to tears. They were over very quickly though and there were several workers in the room who he would go to. I felt the staff members general attitude was really sympathetic to him which is perhaps why the tears didn't last long. They always reported he was happy during the day.
We went on holiday the beginning of September and over this time they rearranged the whole nursery so he came back to a new room with all but one member of staff new to him (the one he knew, he liked luckily). He really struggled with this but I put it down to the change.
However things aren't really improving. Ocassionally he cries up to an hour, though it's usually much less. He is more likely to cry in the day in the new room - for example he was crying over the fact they were going outside when I got him today. And he says he only likes one staff member and he's so attached he cries when she goes for lunch. If I say oh what about Sarah (random name) is she nice he just says no.
Week before last he went for a wee (he prefers to have privacy to do this), I thought they waited by the door but they somehow managed to leave for the dining room without him so he came out to an empty room. It would have only been a couple of minutes I think but still it affected him, his behaviour was terrible that evening and that week really, I didn't know why til he told me 5 days later - nursery didn't tell me at all until I asked. I feel really sad about this but also that maybe that's an overreaction. They were very apologetic when I raised it.
In general I feel staff are more brisk than they were, the one he likes isn't but I don't think she is a strong character. In general it just feels colder. It's not a big room though with a good ratio of adults.
There is space for me to move him to the preschool room in DS2s nursery. They are nice rooms though a little less facilities (his nursery has a huge garden, soft play/ball pool room and hall for PE, here he'd be upstairs but with access to a smaller garden) but I think the staff are warmer in there. I got a nice sense.
I'm so worried about what's best I don't want to cause upheaval for hi, for him to be just as unhappy and he does love the one woman in his room. He starts school next September and I don't know if it's too much change or if it could really boost his confidence. All I know is he has cried almost every drop off for 9 months and it's worse in the new room 
scared to make it worse for him, scared to not change when that's best.
My gut feels the new arrangement at nursery isn't as good but I just don't know what to do.