Hey there,
Congratuations on your impending arrival! We got a City Select when our second baby arrived last year. I have a love/hate relationship with it. I use it daily to commute to/from work with my two kiddos (ages 3.5 and 13 months) on a city metrorail, and for that purpose, it works quite well. It is a smooth ride, I love the hand brake (our former stroller was a graco metrolite, which I love for many other reasons, but hated the cheap foot brake which never held up on the train). If you configure two seats a certain way (back to back), you have TONS of storage underneath in a huge basket. I have the parent console attachment and the child tray (both sold separately but generally worth it). I like to have it in the car with the option to set it up as a single if I just want to put my son in, but also have the double option for if we're doing long walks like at the zoo where inevitably my daughter may decide she wants to ride. it's great for outdoor treks because it has a really good sun canopy. My DD3, who is nearly 40lbs, rides pretty comfortably in it with some room to grow still.
Having said that...the thing is SUPER heavy. I think the frame alone, without seats, weighs over 20lbs. I wasn't willing to lift it into and out of our SUV when pregnant. It *can* fold with one seat still attached, but it's very bulky that way and IIRC, can only be done with the seat in a certain position. With two seats, at least one has to come off before it can fold up. I routinely take both seats off. I'll be honest, I know that the stroller claims to have a multitude of different two-seat configurations, but in reality, I find that there are only a couple of actual workable options. (that leave any ability to put items in the basket below, allow the seats to recline, don't lead to the kids kicking each other in the head, etc. etc....) And, here's the biggie....never in a million years would I take it to WDW. Not only is it heavy and difficult to fold with a seat on (I can't fathom doing the buses with it) but once you put two seats and two kids in it, it does not turn on a dime by any stretch of the imagination. It would be tough to navigate through crowds. When we did Disney in January, we took an umbrella stroller for DD3 and the metrolite for our DS7months. Likely we'll do the same next May.
You mention being offsite with a car, so also make sure you rent a car with a trunk big enough to fit your luggage AND the big stroller!!!
FWIW, if you get the city select, there are definitely a lot of nice features, but to start out with I would just get the carseat attachment bracket (assuming you'll be using an infant bucket carseat initially) and skip the bassinette. It's an expensive feature and often times....babies don't like to lay flat. See what your baby likes before you shell out the extra money for a bassinette when he/she may be totally happy in the carseat, and/or may insist on being held/worn by you! I can't tell you how many times I see parents with uber pricey strollers walking around the mall with the stroller empty and holding their babies in arms
