I'm probably not going to be telling you something you want to hear, but I do LOVE my stroller. I bought the Bugaboo Gecko. Yes it was expensive but, having watched numerous friends go through several strollers with their children, I think we're still coming up at a lower price point and have ultimately been happier.
The Bugaboo doesn't have a tray, but I haven't found a need for it. You can get a cup carrier attachment, but we also decided we didn't really need that. We did buy the bag holder clips for the stroller and love them.
Our stroller was super easy to use right away. We had a bassinet attachment which we would use at home. I could simply put the stroller together and let my baby sleep in the bassinet at home when she was tiny. It was fantastic because I could easily move her around the house with me. We bought the car seat adaptors so we could keep her in her Peg Perego car seat whilst we were out. The car seat attached (and detached from) into the stroller frame with one little click. Bugaboo also sells adaptors for the Graco car seat.
When my baby outgrew her first car seat, we swapped out the bassinet attachment for the seat attachment. The stroller comes with both attachments. The seat is a basic nylon which cleans easily. We bought that little polar fleece zip bag which fits into car seats and strollers, which was genius. I didn't get the Bugaboo brand one because it was more expensive and the other one was perfectly fine. Sorry I'm at a loss as to the brand. It kept our baby warm in her Peg Perego journeys. We didn't really use it once we switched to the next seats because coats and blankets were easier. Plus, she was really into her blanket by that time.
I never have stroller envy when I'm out. I've had many friends comment that my stroller operates more easily than theirs. It has taken a beating and still looks great. There are many options for seating configuration... three seat tilts in both forward and rear facing positions. I can use the stroller with four wheels or two. If I'm on rugged terrain, I can have the two big wheels at the front of the stroller for traction. On regular terrain, the small two wheels are at the front and it turns with no effort using one hand.
I'm currently expecting my second baby and we're trying to decide whether to get a double stroller or the skate board attachment, so my older child can step on and ride our existing stroller. I'm leaning toward the skate board because there isn't anything else out there which I think I'd like this much.