Very interesting idea on the nanny - in our area, two kids will run us over $30K a year in daycare (UGHHHHHHHHH - GAG), so that could be something to explore, especially with the aspect of housekeeping work (maybe even helping getting meals started too?) - I always thought of a nanny as someone who has to be live-in, but I guess there could be one who would work M-F?
The restaurants are a lot of me buying lunch most days - laziness/luxury spend for sure. I've tried to do a better job of bringing/getting free lunch at least 2x a week. With my new WFH arrangement, that will be two days where it will be very easy to eat at home. Not to mention, most Fridays I went out for a NICE lunch (viewed it as a professional development expense, which has certainly paid dividends IMO over the years) that ran $25-35, so glad to have those cut out now (WFH on Fridays).
Groceries are another area where we take into account the cost of our time vs. the task. We use a grocery delivery service which allows grocery shopping to take about 10 minutes a week. While we probably end up paying 10-20% more on specific items, I think we make up for it that we don't buy ANY extra things that are impulsive when in the grocery store (while I'm pretty disciplined when it comes to saving/investing, though it doesn't seem like it from this post, I have NO discipline when it comes to food).
The entertainment last year was out of control IMO, however continues to average over $200 per month. While I'll say no to a lot of extravagant events (and it's easy with the kid where we can't make a lot of things), I definitely don't limit myself when it comes to this category. Concerts/plays/comedians/sports. Also, we put any drinking that doesn't include a restaurant in this category. This is one that I'd like to see average around $100 per month in the future.
Your right on the haircuts (I noted above in my response to @Katrina); Wife has been going to same person since she was literally 5 (26 years), so I think shopping around is out of the question - HOWEVER, she did change her color to go more natural so she promises me this will come down in cost
Alcohol - Ugh, no, embarrassing again. This is purely liqueur store purchases for home consumption. This does include two parties we threw this year however, which were a large amount of the total. We also had a couple of NICE bottles of whiskey thrown in there. With that being said, this needs to get cut in half. We started buying boxed wine the second half of last year and I've been trying to cut weight anyway, so less beer = double positive.
Thanks so much - definitely gave me a lot to think about!