I will try no to repeat anyone and I agree with everything said before me - especially the part that backpacking is not a survival thing - all sound advice.

I am also in a very similar shoes as you, maybe started a few years earlier, but one can never stop learning new things or pushing the limits.

1) Even on day hikes, have enough gear to survive the night if you happen to be lost, sprain your ankle, and it's unsafe to continue. A young couple were lost for 4 days in some very popular park near Los Angeles (with a search party actively looking for them) not more than 2 miles from their car. Look up for "Essential 10 items", you might not need all of them, but you better think about it

2) Map, compass and other gear is not your main asset. Your common sense is. Don't lose it, don't panic if things go bad. People died in the woods from hypothermia while having full backpack of gear. And people survived with nothing for weeks.

3) If you can, starting from June, go each weekend for a 2-nighter, rain or shine. Do the first night near the car and second after a full day hike (return on the second day). Second night is always more difficult than the first, so whenever you can do a 2-nights trip. By next June, you'll probably be very comfortable sleeping outdoors. If you cannot do every weekend, stick to once a month, go camping with your family too, kids love camping, wives love a break from cleaning the house and cooking.

4) If you invest into Ray Jardine's book "Trail Life", you'll probably save a lot of $$ on your gear. And don't listen to REI (or any other store-paid) experts - not even if you take their free classes, their job is to sell to you what they get. If you don't want to buy the book, just check his website. Andrew Skurka's site is good reading too, but Andrew is top level athlete and full-time adventurer, and as such, his gear choices might not be best for you.

5) For longer trips, learn to plan your meals. So, I'd suggest to bring just enough for so many days, as you plan to be out. If you happen to have no food for a day or two, it's not a big deal. Bring more snacks than dinners.

6) For off-trail travel, one needs to practice with map, compass and GPS (and know how to live without it too). Not like theoretically know how to use it, but practice going exactly by the route you planned with a compass in hand, or actually finding your location on the map now and then.

7) As the old saying goes, if it's light on your back, it must worth a lot. But be weight-conscious from the very beginning, especially if it is expensive. I personally prefer a tarp and a quilt summer or winter to a tent and sleeping bag (but I own a sleeping bag now and don't have much funds to replace it) for their weight savings. Even overloaded with so many extras, my bag was not weighting more than 20LB (with food, but not counting clothes worn on my body) on my recent 3 nights winter backpacking trip. So, sometimes, it's worth not to buy the cheapest gear, nor the most expensive one (recommended by a salesman), but the lighter - the better.