I think it really depends on what your kids are like? We had an 18 month gap between our first two and I bought a double pram. OMG, it was so heavy to move with both of them in it and get over the lip of curbs and into shops that had a step. By 2 yrs and 2 months, my eldest refused to get into a pram and would kick his shoes off (meanwhile mum was unaware) and we'd have to double back through the shops to find them. I ended up reverting back to the McLaren stroller for the youngest one (so light weight and narrow and easy to fold into the car) and had one of those kiddy backpack/harness things for the 2 yr old, as he used to bolt near roads. When he got a bit older, he got better at holding my hand etc. I still use the stroller with my youngest who is 2.5 now, and have bought an Ergobaby carrier for number 3 which is due late April. Not sure how I'm going to go with 3 (we sold the double pram on ebay). I'd recommend you buy something secondhand or borrow from a friend, b/c you may not end up using it and pushing two kids can get tiring. Much easier on longer walks to probably get one of those boards that the eldest can stand on, if they get a bit tired on the way back etc.