Start small, especially for the youngin
Make some weekend trips, work up to a week here and there. So much shit goes wrong with gear and such, you'll save a lot of heartache by starting off on short noncomittal trips
Also, leave valid copies of your paperwork with trusted family (not "friends"), half the bums I know cant buy their own beer or apply for work because someone lifted their pack and papers with it.
The cleaner you look and smell, the easier it'll be to deal with society at large. I've worked jobs for months without anyone knowing that I was camped out in the woods, cops dont bother me, etc.