Live in a rowhouse: We started out with an Uppababy Cruz for our first. Then got a Babyzen Yoyo (kept the Cruz). Then when second was born, purchased a roller board for the Cruz. I would wear the baby most of the time or have the older one use the roller board other times if the baby needed the seat. Occassionally we'd bring the kids out with both strollers. Then we purchased a used Vista. It was enormous and we hated bringing it in/out. We only used it for long day trips.

I can collapse the stroller and carry a baby and the Babyzen up a flight of stairs all by myself. So I prefer it over the Cruz for shorter trips. It is also great for the bus and Metro for this reason.

If I was taking the Cruz out when alone with the baby, I'd bring the stroller down the steps and then go get the baby. I'd reverse the process when I got home. I'd plop the baby down in our gated-in space for the baby (babyproofed) and head back out.

Do not leave your stroller outside in perpetuity. It will get stolen. I did it for 2 mins to bring the baby in, and that was bad enough.

Get a Doona.

Mind the size of the wheels and how the stroller bottom is designed, so that the stroller can be pulled up "bump bump" up the steps. Sometimes the wheels are just the wrong size and something is rubbing against the steps and getting worn and ruined.

For a carrier, I couldn't get the "Moby wrap" to work (I'm also short and it's so long!) or the Over the Shoulder Baby Holder sling... well, that's ok but baby might get hot in it. I liked the structured carriers, and my husband would take DD out in it and go walking and talking for a long time with her. The only thing is, they're for 8lb+ usually, so you'll have to deal with other options for the first month or two if baby is on the smaller side.

The advice I got was, look for a stroller that reclines all the way, so your baby can sleep in it. I think that's pretty useful.

Also, when my baby didn't need to be clicked into the stroller anymore, or it was ok to just put her in with buckles, I got a Maclaren Techno XT - a fancy umbrella stroller. It was very light, easy to fold, but still had some under-carriage storage and it lay flat. I used it in airports and abroad; it saw heavy usage. This isn't as good for the first few months but as baby gets older it can be a lifesaver.

Oooh they didn't have anything like the Doona when my kids were little. I would have loved that!