I've given this way too much thought while putting DS to bed tonight.
When my first was born (8 years ago) I had a Graco Travel System. It had a one-handed folding system (pull a button with your thumb and twist to close) that took two hands and a foot to close.
I then bought a double stroller when the 2nd was born. I would have never bought this, but ran into one for $25 on clearance at Target a few weeks before my 2nd was born (when 1st child still loved to ride in a stroller). It was a costco I think. It was actually very nice.
When my third was born, my DH took me to the mall a few weeks after he was born by c-section. DH left the nice double stroller behind the van on the sidewalk when we left the mall.
I was left with my Graco Travelite system. UGHHHH.
Now I love the idea of taking a sleeping baby out of the car and gently placing her into a stroller and then I go off and do what I want. But reality is that the number of times you really want to do that are limited.
Places you don't use the travel system:
grocery store
walmart/target
drug store
church
the grandparents house
a friends house
your home
Places you do use the travel system:
the airport (now I have to admit this is really nice!)
the mall (this is nice too)
the hospital or doctors office when you go back for your post-baby check-up
possibly the paved walking path near your home
Reality is that we use the travel system as a whole package less times than the cost makes it worthwhile. I have never met an experienced mom with her 2nd or 3rd child who loves her Travel System.
We all love it those first few months. Then suddenly we realize that baby is over 15 pounds and when you add the carrier to it it's kind of hard to get baby out of the car without waking her up. Then you just gently get her out of the car and put her in the stroller or carry her.
I'm guessing that by 9 months a good portion of children have outgrown the carriers by weight or height. Then you have to have a good rear-facing car seat anyway. And they are so much nicer and more comfortable for our kids anyway.
Back to the topic at hand. After my son was 6 months, I began looking for a stroller and chose a Mac...based on the advice from the DIS. I also considered a PILKO, and may have selected it if it had been my first child. The Mac is much more portable to me. Compared with a Graco, it takes up half the room if not a third of my trunk, it's lighter, and more comfortable to steer. The only thing I miss: a drink holder. (But my skip hop duo bad holds my drink now).
Okay, like I said, I've been thinking about this too long. PLEASE save yourself the purchase of several strollers over the years and invest in a good one your first time. The travel systems are not worth the money IMHO...unless you can find one that becomes an easy to steer stroller with a heavy toddler in it! That wasn't my experience with a travel system...but improvements are constantly made....
GOOD LUCK...MY LAST

WORD ON THE SUBJECT.