Stroller shopping is just one of many ways to spend your time and money in the big wide world of baby paraphenalia, but as I've had loads of practice (with babies, shopping and stroller-shopping in particular), I thought I'd try to make it a little easier on you as you try to choose your own ultimate stroller.  So here it goes . . .

Start by asking yourself the following questions.

1.  Where do I go?

Examples:  the mall, the grocery store, the post office, the park, hiking trails, jogging trails, neighborhood walks, disneyland, etc

Now, this list will probably change after the baby comes, but eventually you'll probably go back to doing most, if not all, of the things you love to, or must, do.  If you travel frequently, then is it by airplane or car? Also, notice the terrain of the places you go.   Do you take walks or jogs on smooth, maintained sidewalks or on gravel/sand/dirt pathways?  Are the aisles of the stores you frequent spacious or tiny? Do you walk to all the places you go, or do you get in your car to get there?  

The answers to these questions will help you determine the type of stroller you need (we'll discuss types a little later on).  For example, if you frequently travel by airplane then you'll likely want to take a cheaper stroller (in case it gets damaged), and one that's quick and easy to fold down.  If you shop at your local health food store, you know--the one with the mini-aisles--then you'll need to pay attention to the wheel-width and turning radius of the strollers you are considering.  If you frequent unmaintained pathways, then you'll want to look for strollers with durable frames and large wheels.  If you walk everywhere and there are no hills (or you want a great workout), go ahead and get the biggest, heaviest stroller you can afford, but if you drive everywhere first, then you'll definately want to pay attention to weight and folded stroller dimensions.

2.  How often do I go there?  (example:  daily, weekly, once in a blue moon)

If you rarely, if ever, go to a certain place, then it's isn't (IMO) a cost-efficient measure to buy a stroller to fit a need you may never use (ex: buying a jogger because you think you'll start AFTER the baby comes).  Buy a stroller to fit your life.  That said, do keep in mind that although it doesn't look like much on paper, lugging around the weight of a 30+lb stroller (plus kids) IS a big deal.  You won't think about the weight of that big, cushy ride during the store test-drive until you have to start lifting it in and out of your trunk or pushing it uphill with your kids in it.  That's when it really hits your radar!

3.  What kind of car do I drive?  What is the trunk like? 

This question matters more than you might think.  The bigger the trunk, the bigger the stroller can be, but sometimes the shape of the trunk can make certain strollers very difficult to put in.  For example we owned an Acura Vigor when we had our first baby.  The trunk opening is very small and the trunk is wide lengthwise, but very narrow front to back.  We ended up getting a Peg Perego model because it folded up skinny and tall (and was lightweight so I could lift it), instead of Graco model, which usually folds up square.  Also, many people like to put other things in their trunk besides just their stroller, so if you have to empty your trunk to fit your stroller, that's probably a good hint that it's not the right fit for your life.

4.  How many children will need a ride?  (this is important!)

Duh, no brainer you say.  But I needed to accomodate my 2 1/2 yr old and 1 year old, as well as find a stroller that could safely carry the weight of my five year old who still likes the occasional ride.  Let's just say it got complicated.  It's easier if you only plan to have one child, or space them VERY far apart (or are tougher than I am and just make them walk), but I had a friend who planned on having her babies close together and so bought a Phil & Teds E3 before she even had the first baby (talk about planning ahead!).  For those of us in need of more than just single seating, there are still a wide variety of options, but the cost (and stroller weight) jumps considerably, so be prepared.

5.  What type of stroller will best fit those needs? 

I got ahead of myself a little up there, but as far as options, there are single, double and triple strollers and they usually come in umbrella, standard and jogging varieties.  Once you know how many seats you need, then you can narrow down the types, but leave a little flexibility as the next question will also help determine what kind of stroller you need to get.  The umbrella strollers are very basic, lightweight, compact strollers.  I've often seen people buy these in addition to their regular stroller to solve that ever looming question of where is my perfect stroller?  Don't be fooled though, even umbrella strollers can get expensive and they are not as durable or comfortable as the other types.  Standard strollers are usually more durable, more comfortable (adding trays, cups, hood/shades and padding) and have storage.  Joggers usually have permanently angled/reclined seats and three large wheels (umbrella and standard have four, usually small, wheels), as well as many other bonus features.  There are also what I like to call 'hybrids'.  These are strollers that are designed a little like joggers, having big wheels (three or four) and lightweight, sturdy frames, but they aren't really good for true jogging.  My current stroller, the Valco baby Tri Mode with Toddler seat, fits this category (it's an acceptable jogger without the toddler seat, but not a jogger at all with it).  It looks like the current trends may push strollers in this hybrid direction as parents demand an all-in-one, do-everything type stroller.  The selection is pretty extensive for all of these varieties.

4.  What can I reasonably afford? 

Strollers range in price anywhere from a very cheap $20 umbrella stroller - basically the one-use disposable variety (at least for the way we use strollers) - to thousands of dollars for brand-name jogging or elite strollers.  Many parents, as I mentioned before, find it necessary to buy two strollers to fit their needs.  Personally, I'd rather spend more on one really great stroller that's going to last me years, than get two so-so models. On the other hand, I can see how having an extra stroller could be necessary; if for example you're an avid jogger, but need something for around town as well, or if you travel frequently and don't want your nice stroller destroyed by security or the luggage handlers at the airport, you may need to seriously consider buying two strollers. 

Once you've narrowed down the types of strollers you're interested in, do some internet homework.  Look up reviews on the various brand names.  Pay attention to brands or models that get complaints and read them.  Sometimes you find that someone complains about something that wouldn't bother you at all, and sometimes you see that there is a definite pattern of problems with the brand or model.  Just because you recognize a brand name doesn't guarantee quality or long-term durability.  Once you think you've found some good brands, narrow down the models you like.  Once you've got a pretty good idea of what you're looking for, call around the the various baby stores and ask them if they have your stroller(s) in stock.  It's always a good idea to take an actual test drive.  On one of my previous stroller-shopping occasions I had done loads of internet homework and had pretty much picked out the stroller I wanted.  I took my hubby down to Babies R Us for a test drive and was very surprised that the model I had picked handled really poorly, yet another one I'd dismissed handled great.  Feeling the actual weight of the stroller and the comfort (or not) of the handles is a big help in making your final selection.  But beware, as I mentioned earlier, of having a fantastic store test-drive that doesn't reflect the realities of loading the stroller in and out of the car or pushing kids uphill or driving on rough, uneven terrain.

And finally, once you have found your ultimate stroller, don't get caught paying the first asking price.  Most baby stores carry a wide variety of models in stock and can order it the ones they don't have, and many will price match.  The internet is another great way to save money since there are many stroller dealers across the country, but please use caution, read feedback from customers, and even call and talk to the dealers to see who is willing to take the time to help you.  Remember the cheapest price isn't the best deal if you're left on your own when there is a problem.  That said, I made purchases from two different stroller dealers via the internet, and although there were issues with one of my orders it was quickly and satisfactorily resolved.  I've found the employees at the large baby chains to be the least helpful or knowledgeable, but at least then you can fight any battles or make returns in person.  The internet and boutique dealers I've talked to have all been very helpful and knowledgeable and willing to take time with me.  These are the people to talk to, especially if you are trying to find an uncommon or hard-to-find stroller.

Best of luck on your stroller shopping and baby adventures!