Arwin - I've so much enjoyed your posts, picts and videos over the years and it's so clear to so many that you're a guy who just loves his family and makes the most of every opportunity you've got. So happy to hear about the trip south to hog hunt - looking forward to those picts as well!
As far as out of state deals and making it happen, like yourself, I've always tried to put my wife, kids and now grandkids first in every respect whether you're talking time or money. The bear hunts to the western provinces like AB & MB were done with lots & lots of "on-call" at work... My fear, like yours, was if I waited too long, none of it would happen. My advice would be if you can somehow make it happen ($) and you've got the blessing of your wife & family, don't wait too long. Like you've always done, keep putting your family first and you'll enjoy the hunts you do get to go on a lot more. I can't imagine doing a hunt with the thought of "woulda, coulda, shoulda" on my mind. :(
I always referred to some of those bear hunts as "once in a lifetime" events. After having done several of them, my buddies just laugh. :p . Keep working and keep dreaming. You'll get there.
BTW, I've noticed in other posts you're mention of Ontario as a possible destination for a future bear hunt ... PM me if you're interested in the name of a good outfitter at a very reasonable price. I've never hunted with him but I have emailed back and forth with him many times and I've watched his posts and picts on other sites... For a fall hunt, he does VERY well each year.
Best wishes for a successful trip south hog hunting!