You're thinking too long term and you're only going to frustrate yourself in the long run. What you need to be thinking about right now is getting your ratings. Then logging flight time. Then getting on a regional. Then upgrading. Then getting the 1000 PIC. THEN Southwest. I think 15 years is a realistic guess, but it largely depends on what path you take. I have been flying for 12 years and while I fly the KC135 right now, I don't even have 800hrs of flight time. FedEx or UPS are my goal one day, and whenever I think about how long it is going to take me, I start to feel sick. Now I'm focused on getting another 200hrs or so and getting on with a real solid regional (or at least as solid as they get), and one that I can spend the rest of my career there if things don't progress like I want.
Like I said, I've been flying for 12 years, but I was on and off for most of it. If you want to put yourself on the fast track, you really have to plan it out and since you're married, you need to have a VERY VERY supporting and loving wife. She needs to understand that you will likely not see a wage over $25k for almost 5 years after you start flying professionally. It's not going to be easy for either of you.
If I could do it over again, this is how I would do it:
1- Get your commercial ticket as fast as you can, but don't sacrafice quality training for short time. LEARN YOUR STUFF. Get tailwheel time and endorsement while you're at it (see next step).
2- Get a job towing banners at a reputable company. Do a search on this board for one. There are a lot of scams out there. Flying banners is good pretty much only for building time. This works out great as a summer job if youre going to college.To be competative for jobs in the future, you need to also have QUALITY time. You'll find out what that is as time goes on.
3- While youre towing banners, work toward your CFI, CFII and MEI. A lot of banner places have you working 7 days a week all summer, so you might have to work on those ratings on the winter months.
4- After you get those done, get a flight instructing job. When you're searching for one, go to the places you trained previously. They are the ones most likely to hire you. Unless you're a deuche. When you're getting your CFI tickets, you can also use that as leverage to get them to hire you when you are done. Make them sell to YOU.
5- While all this is going on, start looking into the Guard and Reserve. If you get picked up flying with a unit, time building will be slow for the first two years or so, but it's worth it. However, i'ts not a flying club. Service to country is #1.
6- While you're CFI'ing, this is the time to start looking at a regional. Things change on a day to day basis in this industry and the strongest company today, amy have half of its pilots on the street in another three months (seriously, and it's happening now). This is why you can't think too long term. Anyway, pick a good regional, one that pays above the average, where the pilots are happy, good upgrade times and where you wouldn't mind spending the rest of your career. Don't jump from airline to airline, because each time you start our at yr 1 pay and bottom of the seniority - making yourself more likely to be furloughed and most likely increasing you upgrade time.
6- (I haven't made it this far yet) Once you get to a regional, upgrade as soon as you can to start getting your 1000PIC. A lot of times this means commuting, crappy hours/QOL or living in a place that sucks. For this reason a lot of people chose not to upgrade even though they can. Once you get to the upper seniority level FO ranks, life becomes pretty good and when you upgrade, sometimes you flush that down the toilet. Do whats right for you. Also, make a lot of friends, because friends get hired at places like Southwest and can dramatically increase your chances of getting hired by walking your stuff in.
7- Apply as soon as you have mins. Buy yourself I nice set of knee pads and go find your friends at SW!
Hope this helps. It is quite possible that I wasted my time telling you stuff you already know...
ONE MORE THING!!!!!
You and your wife need to have a talk. She needs to know that this is going to be a long, tough road. You need to take a close, no BS look at your marriage and think about if you guys could make it. Just ask how many guys on this forum are divorced from AIDS (Airline Induced Divorce Syndrome). It doesn't have a name for nothing. My wife was a pilot, so she knew what she was getting into marrying my good for nothing a$$

, but I still had a long talk with her over it. I told her that I love her and our children more than life itself and even though I have never wanted to do anything other than fly for a living, if she ever thought that my career was putting our marriage in danger, or if it became too difficult for her to bear, just to say the word, and I would be DONE. (with the flying, not the marriage!

)
All that being said, the most important thing is to have backup skills, where you can find another job if things don't work out for whatever reason. I am learning that lesson right now, since I don't have enough TT to fly anywhere, tons of debt, and no other skills because I have an aviation degree (stupid, stupid, STUPID). If anyone is majoring in this find another major NOW -or at least get another major or minor!
Anyway, my incoherant babble and rants are now over. Best of luck with everything!