Glad I bought:
-
Humanity Family Bed co-sleeping cushion. That thing has been worth its weight in gold.
-An Ergo. Not super expensive but pricier than a Moby or ring sling. I used it more than any other carrier with my first and expect to use it a lot with subsequent babes. And it's the only carrier that DH will even consider now that I convinced him to toss the Bjorn.

-A dresser to store baby clothes and diapers that currently doubles as the changing table. When our babies are out of diapers, we can still use the dresser for storing their clothes. I don't get the concept of a dedicated changing table that has no other purpose.

-A bouncer chair. Has saved our sanity through two babies now. I love mine and don't care that it's ugly and requires batteries to vibrate. It's awesome.
-A Pack n' Play. This has made traveling with a baby about a thousand times easier and again, I don't care that it's plastic and ugly because it works to keep us all happy and sane.
-A diaper sprayer. Cloth diapering would be a lot harder without it and it comes in handy when I'm cleaning the tub!
-A crib that converts to a toddler bed. We use it to confine DS when he needs to nap and can't be allowed to run around the bedroom. When he was really little we used it as a safe place to keep him when we were doing deep cleaning or moving things around. Now that he's bigger and has been expressing interest in sleeping alone, we'll convert it to a toddler bed so he can have his own space if/when he wants it. And it's a beautiful piece of furniture.
-Cloth diapers and extra inserts, and cloth diaper wipes. It was an initial investment that has paid-off handsomely over the years.
Wish I'd bought at the beginning:
-A wipes warmer. My friend told me how much she loved hers but I thought it was frivolous and unnecessary. I was totally wrong and wish I'd had it since Day One. It works so well with cloth wipes and homemade solution! Sorry, DS.

-An
M coat. This ingenious thing is an all-in-one maternity, babywearing, and regular winter coat. A removable panel in front can be zipped in in two ways (big on top for babywearing, big on bottom for maternity) or removed entirely for regular wear. It's well-made, very warm, and comes in cute colors. I got one at the end of my last pregnancy but wish I'd bought it years ago. Awesome!
Wasted money on:
-A swing. Everyone said we'd be glad to have it but they were wrong. It was bulky and huge and loud and ugly and DS hated it anyway. We gave it to friends whose baby also hated it. They sold it almost immediately.

-A breast pump. It was a cheapie manual Medela but still. The bottles were a total waste also. I hate pumping, only did it once or twice, and the baby wouldn't take the bottle anyway. I should have just hand-expressed into a cup and expected it to be spoon-fed to the baby in case of an emergency.
-A Boppy. I hated mine and found it bulky and annoying and the baby was never positioned properly on it anyway. Now it's a glorified lumbar cushion when I sit in bed.
-A dedicated diaper bag or two. How silly, when a handbag with a few interior pockets and a portable rollup changing pad would have been totally fine!
-Baby bathtub. Why bother when I can just bathe with the baby or hold her in the shower?
Glad I didn't buy:
-A stroller. I wore DS exclusively until he was nearly 2yo and got too big for me to carry in the third trimester. Then we went with a relatively inexpensive Keekaroo stroller which has been as good as it needs to be for hardly ever being used.

-An expensive high chair. The cheap $25 plastic Ikea high chair worked beautifully, was totally collapsible for travel and storage, and has held up very well--so well that I expect we'll use it for all of our next babies.
-"Baby food maker". We don't do purees anyway but even if we did, a small food processor and some ice cube trays are just fine.