Three times through. And I think I have it "down".
I've been asked a lot of questions about certain baby items and well, since I've done this thrice and I have learned what works and what doesn't, I thought I would share! Keep in mind budgets differ as well as needs, but I will definitely give you my two cents on what we've ended up with in the baby item category.

Strollers:
So many different needs, so many types of strollers to fulfill them. I have gone through quite the journey with our wheeled friends...I have bought and sold way too many to find the perfect combo for our family...and that I share with you...

What's in my car?

-Combi Flex-it's lightweight, like an umbrella, folds in three, comfortable, reclines, and best of all, has the snack/drink tray for baby led weaning. Necessity when you have an infant in the park needing to eat his or her lunch! Should I mention that it also works with the super-light Combi infant seat? Sold. Not the most attractive stroller on the market, but it's incredibly multi-purposeful! I use it with both Bee and Honey Girl.

-Combi Twin Savvy-In my opinion, the best twin stroller out there (and there isn't anything great, trust me). It's side-by-side, so you don't feel like you're pushing a train, super light, and the folding/unfolding process can all be done with one hand. The infant seat snaps in, and it has the wonderful convenience of a snack/drink tray, which is one of my priorities! Keep in mind, I'm not really out for long periods of time so I don't need large baskets to hold a bunch of stuff in. This stroller is perfect for those super fast trips in and out of the store, the library, etc.

What's in my garage?

-BOB Duallie-My double jogger. Price tag, ouch, however, we justified it because I use my joggers far more than my car! It was used at least 5-6 times a week, so it quickly paid for itself...cheaper than a gym membership! If you're not an avid runner or walker, I would suggest something less expensive, but for a lot of use, this is a fantastic stroller...plus, resale on it is great!

-Mountain Buggy Urban Triple (say that ten times!)-Well, I didn't have much of an option out there as this market is very limited!! I will say that I do like this stroller, it handles very well, for a triple! We got it for an exceptional price used off of Craigs list, the new price is horrendous, but I have to say, in defense of joggers, it seriously is worth the sanity!

Babywearing:

Eek, I've tried a few slings, carriers, etc...some are comfortable and easy, some not. This is what we've ended up with:

-Maya Wrap-(although it's a sling, not a wrap!)...I had a pocket sling, but I learned that my boys outgrew it far too quickly, I didn't like that I couldn't adjust it based on position, etc. and it hurt my neck after about 30 mins of wearing it...with the Maya Wrap, it's a ring sling, it's made from a very soft cotton/linen blend. It's thin and perfect for summer. Easy to wear, easy to adjust, and the best part, it has a padded shoulder that's not too bulky, but does the job! It has a gorgeous tail that can work for covering your babe if they need to sleep, nurse, or if it's cold outside. I prefer to wear this when I'm actually dressed in clothes vs. work out attire as it's super cute (it's quite the accessory if I do say so myself)...it does start getting a bit uncomfortable after an hour or so, though. If you purchase one, try several sites as I was able to find mine for half the price of retail.

-Ergo Carrier-I fought buying one through two pregnancies as I couldn't get over the cosmetics of it. It was just too bulky for my liking... if you're wearing a kid, shouldn't you look cute doing it? Well, yes, but in the end, sometimes comfort over fashion, folks...the truth is, the make up of this product is so practical and, well, ergonomic (hence the name!) that you just have to swallow your pride (at least those of us that have a large amount of it have to...note to self, work on that).
We have used it to carry Bee on our backs, and it is very comfortable, even for strapping a large tank on your back. I found an infant insert on Craigs list and I figured out a way to carry Honey frog-style, which is my preference. I can go all day with her in this and seriously not have any pain or issues. Be honored that I posted this photo for you...I hate taking "self portraits". While you're unconsciously thanking me, do not pay attention to the post-run & park attire, lack of make-up, and sweaty temple--avoid gagging thinking of poor Honey Girl taking in the sweet scent of her mother's sweaty and unshowered state, I think she's kind of fond of it, really...

-Ellaroo Mei Hip Carrier-LOVE THIS! It's so small and compact and can fit in your bag. It's easy to use and I love the way baby sits on your hip allowing both arms to do what they need to do, such as talk very animated, wipe snotty noses, or dirty bottoms--you get the point. I have used it with Bee being 9 months pregnant and it was still very comfortable. Keep in mind you need to wait until baby can sit unassisted, though.

Misc. Neccessities:
-Wooden Teethers- Not made in China, not plastic, not toxic. 'Nuff said.
-Aden and Anais Muslin Blankets/Wraps-These are so soft, so light, and perfect swaddling size. They stretch very nicely and breathe very well. Apparently they are all the rave in babyhood right now, I was given mine as a gift and learned very quickly just how cool they were. Of course they are, they're made out of muslin, what baby wouldn't want to be wrapped in soft muslin (obviously Honey is enjoying hers in the photo below...or just enjoying Great Grandpa's jokes)? Just a tip, go to Target.com...they've paired up with Aden & Anais to create a special brand that is more than $10 cheaper than the original brand.
-Cloth diapers-Quite a few posts on these (click on the label Go Green)! Before you say "never", look into the financial benefits, and you'll quickly change your mind!
-Sheepskin-Post about it here. Still loving it, so is Honey!
-Pump in Style Breast Pump-I worked part-time with Kid and this was super efficient. I haven't had to use it near as much with Bee or Honey, but it has been through some wear and tear and still is pumping away!
-Born Free Glass Bottles- thanks to the BPA-free craze, most bottles and pacifiers are now phalate-free and BPA-free, but you can't be sure (lots of loopholes for these companies and what they can market their products as)...go back to the original, go back to glass!

Well, that's my feedback on the main stuff...please enlighten me on anything else that may work for you...you can also ask questions about anything I have mentioned and I will try and answer to the best of my knowledge.