I guess I was looking for advice on changing the habits instead of just lectures on why the expenses I have are unreasonable to someone else.
Like, how do you throw an inexpensive birthday party with 35 guests? How do you keep your grocery costs down and still eat healthfully? What do you do for fun instead of spending $300 on concert tickets?
Now you're asking questions I can handle.
On parties:
First of all, when it comes to parties ditch the favors. They're just so much clutter after the fact anyway, and it is such an easy expense to cut! Also, hit the dollar stores or food service suppliers for plates, cups, and silverware at better prices than party suppliers. A few balloons and themed napkins or plates, paired with coordinating solid colors for the rest, can set the theme without the price tag of licensed everything.
Also, not cooking doesn't have to mean full catering. Look into party subs, wraps, deli platters, veggie trays, fruit platters, etc. from your local grocer. I don't cook at most of my DDs' parties (sometimes DH will BBQ) but we don't spend more than about $150 on food for 20-25 guests.
Instead of a big, fancy cake, think about a smaller cake and cupcakes in a decorative presentation. We usually get a beautiful 10" round and two dozen "gourmet" cupcakes in a few different flavors that color-coordinate with our theme which ends up costing about half what it would cost for a large enough cake to feed everyone, and the kids prefer it anyway.
Check out Pinterest for game and craft ideas. There is so much you can do with Dollar Store materials and a little creative thinking that there's no reason to spend a ton. An inexpensive craft often makes a nice keepsake/favor too. There's no need for a costumed performer to amuse a group of preschoolers!
Finally, you don't need to throw a big party every year. We alternate between big parties, backyard BBQs, and "destination" birthdays (which are the most expensive despite the smallest guest list!). Last year DD6 just had a BBQ for family and a couple close friends; this year we're taking her and 7 of her friends to our town carnival and fireworks, followed by a sleepover (and it still won't cost $1000, even with the carnival wristbands!). DD13 had a beach party last year at a public beach/park; we got party subs and finger foods and had a great time for about $150. This year she's taking one close friend away for the weekend for the Renaissance Festival, so we're obviously spending more (and might even hit the $1000 mark!).
On cooking:
Look for local CSAs, farm stands, and farmer's markets. You'll find good in-season produce at better than grocery store prices, and you may find that you can connect with a farmer who isn't certified organic (a long and expensive process) but who follows organic practices and essentially get organic produce at non-organic prices. Do the same for any meats that are produced in your area.
If you don't garden, think about starting a small one. I know you said you're pressed for time but your 3yo will probably enjoy the process and even just a few plants of your favorite/most commonly used vegetables can be a money saver as well as a nice way to spend time with her. Plus kids who garden tend to be better about eating their veggies!
I don't actually meal plan. I stock up on things when they're on sale, freeze meats in single-meal portions, and then combine what is in the freezer/pantry with what I'm in the mood for and what fresh produce I have on hand. I also buy meats in bulk when I can - usually a half hog and a quarter cow from local farmers - but that requires a separate freezer in addition to the kitchen fridge. Meal planning and weekly shopping has never worked for me; some weeks there's lots that I'd use on sale and other weeks I end up paying full price for key ingredients to round out the meals I have planned because the sales are processed-food heavy or themed (ie fish during Lent, party food Superbowl week, etc.) to things that don't suit the way we eat.
Outings:
I'm just like you in that. I love my home but I'd much rather be out and about.
Look for free/discount days at local museums. Many do have days when they offer free or reduced admission to increase traffic at off-peak times. Also, see if your public library has activity passes. In my area you can "check out" admission for four to many different places at no cost.
And look into memberships that offer reciprocal agreements. We're members at one science center which gets us half off of admission at museums within 90 miles (and there are three good ones in that range), as well as free admission to many others when we travel. We're also zoo members, which makes a day at the zoo a cheap outing (pack a lunch) and gets us a discount on special events like their trick-or-treat nights and Christmas lights display.
Check out local concerts in the park, and festivals or other special events. It isn't big-name national acts, of course, but superstars don't have a monopoly on enjoyable music. Colleges can also be a great source of inexpensive entertainment; mine hosts plays and touring companies with talented performers at a fraction of the cost of the professional companies that perform at major venues.
Watch Groupon and similar sites for discounts on activities in your area. We've used them for bounce-house places, high ropes courses, waterparks, concerts, festivals, and museums.
And get outdoors. Parks, splash pads, and playgrounds are usually free and endlessly fascinating to young children. And think outside of the "typical". For example, as a family we've taken up kayaking. My 6yo pretty much just rides along, but there are enough rivers and public launches in our area that we can go out often with only the cost of the initial equipment purchase so in the long run it is a relatively inexpensive activity that is healthy too.
ETA: We have a relatively modest income, in the ballpark of half of yours. But we do travel multiple times every year and still save for the future because we're good at keeping the day-to-day relatively inexpensive. Part of that is setting up good habits and expectations in our kids from the start and your DD is at a good age to start doing that. You could teach her that huge birthday parties with costumed characters and elaborate themes are an every year event, and that dinner is whatever you're in the mood for at the moment, and that outings have to be $300 concerts... but that's just going to escalate as she gets older. Or you could teach her that fun can be anything from a free concert in a park to an affordable day at a museum as well as the occasional high-priced event, and that birthdays can be celebrated simply and be just as much fun. In the long run, I think you'll be happier as well as financially healthier if you instill an appreciation for a wider range of experiences, including the cheap/free, in your child.
