This post is based on my experiences with the strollers that I have used and also on my lifestyle. There are many other strollers out there that I have not tried before so I may have missed out on newer versions of strollers. However, I do feel that choice of strollers will eventually boil down to weight and how you intend to use it, and of course the price. We owned a:
Peg Perego P3 Pliko Compact (8.5kg);
Jeep Wrangler All Weather Umbrella Stroller (4.3kg);
Silver Cross Reflex Pushchair (8.5kg);
Summer Infant 3D Lite (5.45kg);
City Select (12.7kg)
With 2 upcoming baby fairs, you are thinking about getting a stroller but not sure what you should get. Well..I’m no expert on strollers but after ‘collecting’ some strollers and decluttering, here are some views of what you should consider when you are getting one:
1) Your mode of transport: Car / Public Transport (Bus, MRT) / Cab
Depending on your mode of transport, you may wish to consider the following:

Summer Infant 3D Lite
Weight:
Weight of strollers can range from 4kg to 12kg. This is probably one of the major considerations depending on your mode of transport. If you travel by public transport (bus, MRT), you wouldn’t want to be lugging a stroller that is too heavy. Obviously, the lighter the stroller, you will be giving up another aspect of the stroller such as the size of the basket, counterbalance, flexibility to recline and canopy cover.

Jeep Wrangler All Weather Umbrella Stroller
Ease of folding: One hand-fold
Umbrella strollers are usually the easiest to fold. With the Silver Cross Reflex, Summer Infant 3D and Jeep stroller, it was so easy to fold. Just kick a latch and fold it downwards. Unfolding it was just as easy as releasing a catch and unfolding. There are other one hand fold strollers like Combi strollers as well. So important when you are rushing for the bus, or travelling solo with two kids.

Peg Perego P3 Pliko Compact
Standing: Can it stand folded?
With the Peg Perego, we found that having the stroller stand on its own after it was folded was a major bonus. We didn’t have to hold on to it after it was folded. Of course wheels can be locked to prevent some strollers from rolling all over in the bus, but it still meant that you would still need to hold on to it. We did learn that technically speaking umbrella strollers could still stand on its own but it also meant that you would have to ‘balance’ it on its handles (upside down) to make it stand.
2) Long term investment: 1 stroller for multiple kids!

Baby Jogger City Select
If transport is not an issue, the number of kids I can squeeze on it would be my next priority. We were sold on the Peg Perego on the basis that there is a toddler bar on the back of the stroller. The counterbalance for the Peg Perego was impressive. The salesman had stood on the toddler bar without the stroller tipping over! Sold! It is our first stroller and we are still using it for 3 kids (2 kids on stroller, 1 kid in baby carrier). Obviously the downside is that if seated kiddo in the stroller wants to nap, the one on the bar will have to walk. So it really depends on the napping situation. Otherwise, really good ROI without having to buy a double stroller.
Alternatively, you can consider a stroller like the City Select. I love that it can be configured to multiple seating arrangements. Bassinet for the baby, seat for the 3yo and a glider board for the 5yo. Total weight: around 40kg. OMG. Definitely gives me a good workout. But hey, it also meants I don’t have to carry anyone. Haha. Downside: you won’t be able get on a bus. Even fitting it into a cab is going to be tricky with a bassinet and a seat. Basically it is the type of stroller you wouldn’t even think of folding once you are out of the house.
Obviously there are other options of double strollers like the Maclaren side by side, Contours and Joovy tandem strollers which are definitely way cheaper than a City Select. But I guess I really liked the idea of having the glider board as an option to include a 3rd kid.

Silver Cross Reflex Pushchair
3) Going shopping? : Counterbalance & access to basket
I only learnt about it when I spotted a friend’s Maclaren stroller. It was a nice sturdy umbrella stroller. But if the bags behind weighed heavier than the weight on the seat (empty or occupied), the stroller will tip over. And I did learn that the hard way with the Jeep stroller especially. While umbrella strollers are lean, the downside is not being able to hang much stuff on the back of it. Which means don’t happily pile on the shopping whilst kiddo is in it and then take kiddo off the stroller! I really enjoyed the Peg Perego cos of the good counterbalance. I really didn’t have to worry about tipping strollers.
Other downside to umbrella strollers is the accessibility to the basket at the bottom. I’m sorry to say the accessibility for my umbrella strollers SUCKED big time. The kids and I go out a lot, so this means we abuse the strollers a fair bit. Heading out with 2 kids means diaper bag plus carrier plus what-nots. Diaper bag hangs off the handlebars, everything else goes into the basket. Good enough, IF the seat is never in recline position. Once the seat is in recline, you can pretty much forget about putting anything bulky inside the basket.
For a single stroller, I love my Peg Perego basket. *smooch smooch smooch* Nuff said. Hahaha.
4) Pushing it with one hand: Yes, handlebars make a difference!
It took the last stroller to my ‘collection’ to realise the difference it made to have a U-shaped handlebar, compared to having two handlebars to push. It is so-so much easier to navigate single-handedly with a U-shaped handlebar! Obviously there are some physics involved which I do not know how to explain. Trying a stroller empty, versus a 15kg weight inside will make a world of a difference.
Conclusion:
I head out with the kids alot and well, counterbalance is the last thing I want to worry about when I am out with them. Weight was not an issue to me as I lived close enough to a train station so if I couldn’t fold and lift it up the bus, I could always walk to the train station. Space, and usability was definitely a priority. Best if I could use it for up to 3 kids, but alas..let’s not abuse a single stroller lah.
For me, the Peg Perego best fits my lifestyle with 2 kids. Usually I’ll piggyback one kid and lift the stroller up the bus whilst holding the hand of the other kid. At 8.5kg, it is manageable. On ground, older kid goes on toddler bar, younger kid goes on the seat. The basket is big enough for me to easily toss stuff inside, regardless of whether the seat is reclined or not. Unfortunately, manoeuvring it single-handedly is a pain but I don’t do it that often. It is of a decent size, a little bulky but doesn’t take up too much space in the boot of a sedan.
The Jeep is good for really short trips to the shops or market. The type with no anticipated naps as it doesn’t recline.
The Summer Infant 3D was our travelling stroller. It was lightweight enough to carry around easily, didn’t take up much space in the car boot and could still recline almost fully to allow for naps. Counterbalance was obviously crap but as long as a kid was seated inside it, we could hang our shopping haul! hehe.
Silver Cross Reflex is a bonus. We loved that it is an umbrella stroller that could allow for reverse facing and still fold neatly (ooo I really miss that plush baby nest!)
The City Select is our go-to stroller if the kids and I head out to town or go out for long hours at the zoo. Everyone gets to be on it, it is easy to manoeuvre and still has decent enough storage in the basket (depending on how you arrange the seats). But it takes up A LOT of space in the boot. Surprisingly tho, we managed to fit a City Select (with bassinet only) plus a City Select mini in the back of a Toyota Prius. Well, not in the way I liked it but it fits. So there you go.
Hope this provides you with some insights on how to choose your stroller!