I wouldn't go for a side-by-side as you're then stuck with an empty seat when your older kids decide they don't want to ride in the pram any more. At least with a normal pram, you can just remove the toddler seat when it's no longer required. Just a thought.
My pram (the Baby Jogger City Elite) is fantastic but it's more than you wanted to spend, around $1000.
I have valco runner with toddler seat, it does the job, a bit awkward when walking on slopes as the wheel has to be locked in position or the whole thing tends to tip if both kids are in it. I didnt like the idea of having a child so low in the phil and teds but that was jsut me know a lot of people love them. One problem witht he valco I have is the toddler seat has no sun cover (you can buy one but its more money). The toddler seat doesnt recline but my dd's wont sleep in the pram anyway. Can be tricky to get large items in the basket when it is fully reclined.
I have found it heaps easier to put bubs in my mei tai and dd1 in the pram, or trolley if we are shopping. DD2 loves the mei tai and generally falls asleep in 15mins in it.The new pram has really been a waste of money for us as Ive used it half a dozen times if that. DD2 is getting a bit heavier now so Im using the pram occassionaly or her but dd2 is almost three and is wanting to walk more often than not
I have a Phil and Ted which has been unreal. I can go shopping with the two of them and not worry about fitting down isles and I go walking all the time. I felt the same about the bub in the back, but my boy doesn't seem to mind and my little girl also like to go in it sometimes (she thinks it's fun). Without it I wouldn't get out by myself with them nearly as much. The attachment seat can go under when the bub is old enough or on top for the toddler when the baby is new. The only annoying things I find are the straps to put it up and down, I was spoilt by my beema which is so easy.
I was going to sugest a baby carrier for bub and then todler in pram. I have a 13.5 month old and she rarely goes in the pram as I carry her alot, mainly on my back now but it is great so that I have two hands free to do things with my older kids. She started out on my front when little but still alowed me to do things with the other kids.
We do the sling thing but I'd like the option to be able to put DD3 down if required. Plus I exclusively used the sling with DD2 and now she hates the pram.
I have a 3yo and 9mo - I think all of the suggestions are great, it really helps to have others perspectives. FWIW - we have the double Mountain Buggy and Maclaren Twin Stroller. I wanted to walk daily so the MB stays up at home and the Maclaren stays in the car. My 3yo walks in fits and starts - her spirit is willing but we do quite big walks so she hops in and out etc. The MB only just squeezes into my boot (Commodore Stationwagon) also and is quite cumbersome but fab to 'drive'. I bought both doubles with the intention of reselling on ebay to recoup some $$ when we were finished as they are both generally in demand. The girls love being side by side and chatting,playing etc. Happy shopping!
We bought Phil and Ted dash as we planned on kids close together!
I have loved phil and ted with only 1 child but I must say takes up lots of boot room so I use it for walking and my stroller lives in boot of car but that will all change when bubba 2 comes along, will be getting toddler seat for Phil and Ted.
My friends who have phil and ted with 2 kids all love it!
Its a bit on the pricey side, but thought I should mention it anyway.
Have you checked out the ABC adventure buggy with toddler seat on top? They also have a reclining newborn toddler seat - so the new baby can face Mum at eye level and lie back - whilst the older child faces outwards underneath. Or you can go for the regular toddler seat up top for the older child, and have the baby sleep in the bottom part. I think this is great as neither childs view is blocked by the other.
Its traditionally a 3 wheeler pram like the mountain buggy, but comes with an optional
4th wheel for extra stability (most people find they dont need it).
So the pram is the width of a single- good for shopping etc - but it is also fabulous for outdoor terrain, and can easily convert into a single pram by removing the toddler seat.
There is a huge basket underneath which has a zippable cover to protect your items.
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