PP, what is the business?

What are your interests? Do you want to work for a company or work from home with a flexible schedule?
I was a successful corporate trainer for 12 years, then reached the pinnacle of my career after starting my own company 3 months prior. I ended up retiring from corporate america to continue to build my own business because I wanted something more flexible and my PT business had grown into something that allowed me to do that.
I’m working with stay-at-home dads and moms like you who need to contribute to the family finances and want something of their own in addition to raising kids. They’re
building lucrative, fun businesses in part-time hours while still being there for their kids and families.
We're in the process of expanding in the DC area - we're actually part of a $6 billion global brand. Our Corporate Chairman will be in Chantilly this weekend, March 2 sharing more!
I'm more than happy to share more. Let me know.

I read on the public school boards that Hearst (Ward 3) may be starting a ps3 program starting this September, so definitely follow up on that.

Is there some reason OP simply must avail himself of public PS3 in DCPS and therefore be a slave to those hours / that commute out of his Ward 3 'hood?

Why not pay for preschool in Ward 3 with wrap-around care. Adas Israel's Gan just started one on Porter and Conn Ave. Also Franklin Montessori. Communikids. Friendship Children's Center. Broadcasters Child Development Center.

There are many ways to avoid criss-crossing the city for a 3s program. Of course, it will cost you. OTOH, with both DH and DW working, that should be doable for one or even two years.

OP, I get it. I'm a long-time SAHP in Ward 3 myself, trying to get back to work and I'm having confidence issues. But, don't box yourself in re: the lottery = "free care!" thing.

OP, I second the advice about getting a job first and figuring out the childcare later. I don't live in DC, so I can't get sucked into the allure of free preschool, but I do know that my DC-based daycare center is under capacity for its 3yo room. So if you find a job, you will have multiple options for childcare (the DCPS/charter route as well as private centers). Focus your energies now on figuring out what you want to do and how to get a foot in the door. Unfortunately, there's little guarantee you'll get a job right away - I realize that's probably not what you want to hear, but I also imagine that when you're dealing with so many uncertainties a little time to figure things out may be welcome. Good luck!

Don't sweat the credit check. Most companies don't do it unless you're going to be managing finances and if they do run a check it should be contingent on a job offer so even if its bad they'll likely be understanding if they want to hire you. Don't let them run one until you're close to an offer and when they do explain what happened. I wouldn't hold that against you.

OP, I know how you feel. I have been a SAHM for 11 years. I tried applying for some jobs, but didn't get any interest whatsoever. So, I've started my own business re-purposing furniture. I find my items at thrift stores and estate sales, and sell them at a few shops in my area. It's a lot of fun. I don't know if this is something that interests you, but maybe there is something you can come up with to do on your own while your daughter is in school? I grew up with a guy whose dad started mowing lawns when he lost his job. 35 years later, his lawn/landscaping business is still going strong and grown significantly over the years. And his son is now a co-owner. They are both doing quite well. Good luck to you. I know it's difficult.

What about working as a school substitute? Good way to get your foot in the door, build your resume and you can pick up assignments as your schedule allows.

It seems I know a number of SAHM moms that do this once their kids are in school, and some just get PT/FT positions at school. Seems to work well with school holidays/breaks and matches the school hours that negates the need for regular child care.

I had this debate a year ago- my now 3.5 year old could have started DCPS PS3 in September, but he was not fully potty-trained. I had been home with him pretty much one-on-one for that whole time with part-time nanny help during the second year.

This year I got a teaching job in MCPS, about an hour drive from my home. If I don't leave the house by 6:30, I won't get to work on time. That left the issue of getting him to preschool at 8:45 (or whatever) and then not being able to get all the way home to get him at 2:45 (and with DH's schedule, there was no way he could do that).

Even though the idea of the free care was so enticing, we ended up opting for an in-home daycare close to my work. It's $275 / week, and for now fits our purposes exactly. I just couldn't figure out a way to make the DCPS thing work out. And the fact that he wasn't fully potty trained at the start of the year helped me make the decision.

Good luck. It's so hard!

Get a job now or as soon as you can, use the money to pay for second (used) car and daycare or a temporary nanny or daycare to get yourself used to the routine. Be ready to give up your free time on weekends or whenever your wife is available to help, to run errands like grocery shopping, kid's shoes, house cleaning etc. Finding a good job will be possibly harder than hiring a nanny or getting into a good school in the lottery. BTW you are going to have a hard time getting into the better DC PS-3 programs because there a lot of siblings and proximity preference for locals who live near the schools (like Capital Hill or Petworth.) Take some time NOW before you get that job to personally visit all the charter schools you plan to apply to. There is no guarantee you will get in to any of them but there is no limit on the number you can apply to, so you might as well apply to a lot. By visiting you will be better informed and not be in panic mode if you have to choose between two charters, or get off the waitlist for one while considering another.
Next year you will be in a much better position financially and emotionally. Unless of course your wife gets a huge raise and you are able to stay home full time.

What exactly is DW schedule? Early, late, long days, travel? Why is she completely out of the picture?
Something to consider: a non-9-5 type job. I WOH M-F, fairly traditional schedule albeit shifted early. DH works a totally wacked out, late mornings but late nights, weekends but has off weekdays, schedule. Parts of it SUCK but parts are great. Such as MLK Day, which we don't have off work but daycare is closed. DH just switched his day off that week and VOILA problem solved.

I think you should get out there and start looking to see what jobs will work for you. It's entirely possible you won't have a job by the time school starts anyway right? Most dual working parents manage child care issues - you can have a sitter pick your child up from school and watch her until 6 or 7, without doing after care. If you have a job, perhaps you and your wife would be able to trade off drop-off.

Also, with free PS, this may be a great opportunity for you to get your foot in the door as an intern somewhere for 6 months, get some good references, and still work during only school hours. It's hard to comment on the job market w/o a clear career path outlined, but I think there are ways to work out the child care problem if you do need (and want) to work longer hours.

Would you be able (or want) to train for a new career that interests you more than, or could help you make use of, your business degree? It seems like you are in a good position to just head off in a new direction, away from what you see as your past missteps.

Regarding drop off and pick up: do you know anyone with a similarly aged child? Or even just someone at the same school you're looking into? Could you work with that and carpool? One drops off, one picks up.

Man here.

I've stayed home with my daughter for three years. God willing, she'll start a PS3 program somewhere next year. I'm in a precarious position and would really appreciate help navigating it. I'm 30. If you factor in college and over three years of unemployment, I don't have much work experience. And if that weren't enough, I filed bankruptcy a few years ago on over 200k worth of medical bills from a surgery that was deemed pre-existing. Sadly, my degree is in Business, so my credit will probably nix any chance of a job in that realm. For all intents and purposes, I have screwed up my life. But as a parent, I read a very good self-help book by a certain Dr. Seuss who wrote, "And when you're in a slump, you're not in for much fun. Unslumping yourself is not easily done." I'm trying to unslump myself.

With my wife's work schedule, I already have the life of a single parent. I don't know how to get her in school and get a job at the same time. The whole lottery process causes so much uncertainty. I don't know where she'll be in the city. We live in Ward 3 and there are no PS3 programs here, so it's guaranteed that she won't be close to home. I'll have to drop her off and pick her up, which means that I'm limited in where I can work. With my checkered past, I'm not exactly in a position to negotiate or make demands. Even with extended care, I figure that I'll still need to get in no earlier than 8 and out no later than 5 in order to pick my daughter up on time.

How do you do this? How do you keep all the pieces in the air? Is it even realistic to assume that I'll get a job anytime soon with my history and this market? Knowing that I'm the primary parent and that FMLA doesn't kick in for at least a year, how do you handle days when your kid is sick? I feel like a great parent, but a horrible adult.