I'm probably not the best person to answer; we have three buggies and they all get used each week...
W have a BabyJogger City Select - this replaced our original travel system (M&P) which we had for DC1 until DC2 was born. The City Select is a tandem/single. It's big, it's robust, has a massive basket and can be parent-facing. DC2 is 2 next month and this is still our everyday buggy, still in parent-facing mode and I love it. In fact, the main reason we bought this double was because DC1 was 2.7 when DC2 was born and refused to face out...
We also have a Maclaren umbrella fold. It lives in the car and is great for short trips to the shops, using on the tube/buses (though for a full day out in central London I take the City Select) or taking on holiday. I rarely use it for DC2 to sleep in, though - whereas he will climb into the City Select for a nap! It's light but horrible to steer and can't be pushed one-handed, unlike the City Select, so I hate taking it anywhere I need to hold onto DC1’s hand.
Finally we have a Nipper 360 3-wheeler. We use this for hilly/off road walks, mud, snow, etc. We had this for DC1 - my parents live in the countryside, DH's live by the seaside, we live near woods/steep hills. It's suitable from NB, our Maclaren is suitable from 6m and was easier for holidays/tubes etc once we had a toddler as well as a baby. We use this least of all these days, but it came into its own last winter, being pushed uphill for just under a mile each way twice a day on snow and ice to nursery and back. It will go where the car can't, and where a four-wheeler will get bogged down, so it's my emergency back-up.
I would love to get rid of a buggy. At the moment, we do use all of ours every week, and not one of them would be suitable for all purposes. So for now we're hanging on to all of them rather than compromise for the sake of another 6m or so. In fact, we even used the City Select as a double again a month ago, when DC1 was ill, the traffic was totally screwed and I needed to get her to the GP a 20-min walk away...
So basically, you're never going to find the one perfect buggy! You need to work out what you're most likely to use it for on a daily basis and for how long (and whether there'll be a DC2 within the next 3 years), and whether you are going to buy just the one buggy or be prepared to buy two for different functions, eg cheap umbrella for holiday if your main one is expensive, etc.