Should I or shouldn't I???

I'm contemplating going back to work. Last time I went back to work, I put work before my family, worked way more hours than I was supposed to, and was very miserable - busy all day long cleaning up everyone else's mess. But, I'm tired of having to balance the checkbook and clipping coupons, not going on vacation, and having debt that I can't pay off. Here's my list of pros/cons:
Pros
1. I'll have money: Don't get me wrong, Jay makes good money, but I miss the days of being able to buy whatever we wanted, whenever we wanted. I never balanced the checkbook and we always had money in savings for vacations or whatever. Besides, Isabel starts school next year and I really want to be moved into a different school district before she starts.
2. Isabel will be in daycare/preschool: This is a pro because she loves being around other kids and I just can't find a playgroup/mommy group that I like.
3. I can payoff my medical bills/credit cards: This would be great. If we didn't have the medical bills or credit card (just one thank God), we would actually be pretty well off.
4. It'll build my resume: OK, stupid pro, I know, but hear me out. Last time I went back to work, the question I always got was why was I out of work for so long. I hated having to explain that one.Also, if something should happen to my dear Hubby, I would be able to pick up the slack or take care of my family.

Cons
1. Noah will be in daycare: I hate putting my 6 month old baby in daycare when he is unable to tell me if anything is going on that I should know about. Plus, I'll miss out on some of his milestones.
2. Stress at work: I hated having a boss when I went back to work. I've enjoyed relaxing at home with my kids and not having anyone to tell me what to do.
3. Stress at home: Hubby was not happy when I went to work last time, although he didn't mind the extra money. I was always going in earlier and working later than I was supposed to, and being salaried, didn't get paid extra (hmm, sounds familiar...).
4. Pay sucks: It is so hard to find a job right now that pays enough to cover the added cost of 2 in daycare, extra fuel cost, extra clothing cost. They want a 4 year degree with 5 or more years experience, want you to be bookkeeper, office manager, HR and don't want to pay more than $30 a year.

So, should I just stop being materialistic and be happy being a mom or should I try to contribute to the family to reduce the stress off my husband?? Just don't know...