More seriously though,
(1) “another mouth to feed”? Wife might want to breast-feed; I did it for 18 months while working full-time; definately worthwhile both financially and personnally for this single mom. Also, kids really don’t eat a lot on their own unless told to ‘clean their plates’. On the other hand, cleaning supplies bills will go up. Toddlers don’t actually eat, they absorb nutrients via osmosis through their skin.
(2) “clothe”? Nah – skip the cutsie outfits or let grandma buy them, My boy is 5 years old and all I have purchased for him is underwear, 1 swimwuit, and socks. Ok, ok – he’s the only grandbaby and grandma loves to buy his clothes; however, we always go to GoodWill shops or yard sales. In your case, there will be handmedowns which kids don’t mind wearing (particularly if they hero-worship their older sib) until they are much older. Semi-nudity is perfectly acceptable to young children at home. In fact, even if they start dressed they end up wearing only a diaper, 1 sock, and maybe a t-shirt. Babies are easier, cheaper, and much more fun to clean than clothes.
(3) “house”? What?! You’re getting a second house just for the baby? Trust me, s/he won’t like living alone for about 14 years. Actually, any additional housing costs incurred by the presence of more than one person are incrementally smaller. Unless one sleeps with the window open and the other turns the heating full up.
(4) “insure”? Same principle as for housing, most health insurance increase only slightly for additionally people. My insurance, for instances, has a ’single person’ rate and a ‘family’ rate — no matter how large the family. Makes me think about adopting just to get my money’s worth.

All-in-all . . . Congratulations.

The way I see it, #1 and #2 are well loved and thus well worth the money and thus not bad financial moves. Unless you could have figured out a way to save on #2 without undue time and trouble.

For #3 and #5, you could have guessed better in playing the market or you could have guessed worse. Sounds like you did fine to me.

For #4, again you feel you are getting good value. But like another commenter, I am wondering why you think people talk more when out. Is it because you would be busy cooking at home? Maybe you can think up a way to make cooking at home work better for you.

As long as you are happy with your purchase is all that matters. Sometimes you get what you pay for. And when it comes to computers, the expensive route is better than the cheap route. At least we don’t pay what they used to be (back in 1994 I paid 2.5K for a pc tower with memory that can’t even hold an iTunes playlist).

My worst mistake – purchasing plane tickets for $250 each ($1K total) and then seeing the same tickets a week before our departure for $100.00 each. I could have cried – actually I did cry.

LOL, that reminded me of the first few pages of Peter Pan where Mr. Darling is trying to calculate whether or not they can afford to keep each of their children:

“For a week or two after Wendy came it was doubtful whether they would be able to keep her, as she was another mouth to feed. Mr. Darling was frightfully proud of her, but he was very honorable, and he sat on the edge of Mrs. Darling’s bed, holding her hand and calculating expenses, while she looked at him imploringly. She wanted to risk it, come what might, but that was not his way; his way was with a pencil and a piece of paper…”

:D One of my favorite passages from that book.

In terms of buying the index fund and the cat food/litter, good luck trying to buy it when it is at the low. Unless you have some sort of psychic ability that the rest of us aren’t aware of, I’m not sure you can really blame yourself. Hindsight is 20/20, nobody’s ability to predict the future is.

Anyways, keep up the great work on this blog.

I own a Mac and probably wouldn’t recommend buying one if the majority of stuff used is Office. I spent $1300 on mine and only use Quicken, Firefox, iChat, and a few others. I knew I wouldn’t use it to its full potential, but i’m only 24 and my friends would have dis-owned me if I bought anything else than a Mac (semi-kidding). If the Vaio was over a grand, then yes- a Mac. If under $1000 then it was a solid investment. Speaking of bloatware, 1 gig is wasted on my mac from GarageBand. iCal is a waste, .mac is a waste, not to mention you have to pay for .mac or whatever it’s called.