I am kind of late on this post, but better late than never. I think you are in a bad position. You say you are losing sleep over this decision, so I would like to give you what I believe is good advice.
In retail you can make 95-120k right out of school, depending on your location, maube a little more maybe a little less. Chances are you can bag a sign-on bonus as well (being realistic say ~10k). At your age, your decision to go to pharmacy school was probably based on this: you needed a good-paying, secure job. This is even more of a need for a man with a family than it is for most. Residents will always get paid about 30k. Any less and you couldn't live off of the money, so I think its afe to say that residencies will always pay about ~30k (plus inflation of course...). On the other hand - right NOW, the market for pharmacists (non-residents) is HOT. This WILL NOT last forever. I am a PY2, and I study finance in my spare time. I read only from the best investors, and one thing is true - bull markets are NEVER permanent. From what I have read, pharmacist wags were rising at 6% per year and are beginning to taper off to more closely match 3% (normal inflation in a solid economy - which is not what our economy is now, but you have to assume our economy will get back to normal, or you will drive yourself crazy trying to predict what will happen.) You have to look at this decision with the right priorities in mind. You have a 6 figure debt, a wife, and 2 children. Your first responsibility is to them - to provide security (financial security is one aspect of security) for them. Job satisfaction HAS to be secondary.
I understand that residencies have their appeal. What it boils down to is job satisfaction (respect, diversity in activities, and many other positive factors). But you also must consider who is exposing you to the idea of resdiencies and WHY? 2 institutions always try to sell the residency. 1 - your school, and 2 - the place offering the residency. WHY? Your school's reputation is enhanced when it's graduates have board cert. and residency experience. YOUR reputation is THEIR success as much as it is yours. The place offering the residency gets this: bonified PharmDs working at Tech wages. Actually, maybe less than tech wages when you consider that pharm. residents can work 70 hours a week (+/- 10 hours, + homework?). Right NOW, pharmacy wages are near their peak - don't miss the gravy train, man. Snatch up that high salary, get a sign-on bonus, work for a couple of years (and only at ~40 - 50 hr.s a week), pay down that debt, then think about a residency. Over that time you can ponder the decision some more, and it will be less stressful since you will have a proactive approach toward your debt, and feel less rushed about the decision. Patience is a virtue. Never make a decision in haste or out of fear.
You said, "Please lead me down the the straight path..." I got the impression that you believe that a residency would be the straight path. Maybe, maybe not. The FACT is that this is subjective. Both roles, clinical and staff, need to be filled. We have all been romanced with the valuable role the clinical pharmacist plays, but staffers are just as - if not more - important. You NEED someone to get the drugs out safely in a timely manner. Look at small, low-budget hospitals. When its crunch time, there is always a staffer left and the clinical guy gets the ax (just ask GravyRPH). Just, don't think that staff pharmacists are less important. Yes, their jobs are slighlty less glamorous, but sometimes that's the more noble route.