My two two oldest sons and I are planning a 2 day trip over Labor Day weekend. It will be a combo of BP'ing and car-camping. We are slowly adding to my inventory of gear as funds allow. We plan on some multi-day trips as we get further into the fall.
"As funds allow" I hear you; everyone has that constraint. Just looking over your list, it looks like you'll be spending a lot of money in order to gear up for both 3 season and 4 season BP'ing & camping. One thing you might think about: Instead of immediately gearing up for both 3 and 4 season outings, gear up for just 3 season for now. If you gear up for both, you'll have to buy cheaper gear that you'll wind up wanting to replace in a year or two. The lesson I've learned over time is to buy gear that's really going to work for me. Otherwise, I wind up with gear that I don't like and doesn't work well for me, and I replace it in a year or two.
Buying twice does not save money. Buy the right gear the first time if you possibly can.
I don't know where you are, but many outfitters will have rental gear. I'd rent first, really get an idea of what I like and what works for me, and then buy. Just some thoughts.
Here is what I have so far:
Osprey Talon 22 (for day hikes… also volley with a SAR team so it also is my search pack)
Good pack; I've got the next size up. The 22 is pretty small for an overnight pack.
Cabelas two-man tent with rain fly (bought used)
Well, if there are three of you, you may need another shelter. Again, I would rent first if possible (I have no idea what's available in your area). Another option, depending on where you plan to hike and what conditions you'll face is a tarp. A tarp will be far lighter and cheaper than a tent. A large tarp should accomodate all three of you.
Items I will be ordering this week:
MSR Dragonfly stove
The MSR Dragonfly is a good stove (I've got one), but it's heavy and expensive. You might think about other alternatives. If you want a 4 season stove that you can use all year, a liquid fueled stove is a good choice, but I might go with the MSR Simmerlite which is lighter and cheaper.
I started out with a liquid fueled stove and used it for everything (all seasons) for a number of years. Eventually, when I could work it into the budget, I bought a canister stove. A canister stove is far lighter (and generally a lot cheaper) than a liquid fueled stove.
So, buy a liquid fueled stove now but don't get the D'fly; get something lighter and less expensive. When you can, buy a canister stove for 3 season use.
Eureka Cheyenne sleeping bag (40+ degrees)
The Eureka Cheyenne at 2.75 pounds is a pretty heavy bag for a 40F degree bag. My 32F bag weighs 1 pound. You'd be carrying about 3 times the weight for a lesser bag.
Bags are a good thing to rent until you can put together the money to buy a bag you really want. If you stick with backpacking, you won't stick with a cheap bag like the Eureka Cheyenne.
If you really want to buy: Sleeping bags are expensive, so maybe the Eureka Cheyenne is the best you can practically afford, but I'd shop around first. Cabelas in general is a store I'd steer clear of for backpacking gear. Nothing wrong per se with them, but Cabelas is more geared to hunters and fishermen. Gear for hunters and fishermen is generally much heavier than that for hikers and backpackers. What Cabelas calls "lightweight" is what we call "heavyweight" here. Seriously. When you see "lightweight" or "ultralight" on a hunting or fishing site, disregard it. What's lightweight to them is something most of us here would never even consider buying.
If you really want to buy rather than rent, here's a couple of sites (there are dozens of others) that you can get cheaper gear at:
http://www.campmor.com
http://www.SierraTradingPost.com
Cabelas XPG sleeping pads
Again, I'd generally steer clear of Cabelas. However, these don't look too bad. If you need to buy 3 pads, that gets pretty expensive if you get the good ones. However, note that these pads are the self inflating variety. Self inflating pads, in my experience, are more comfortable but are heavier than closed cell foam pads (like the Thermarest Z-Lite for example). I personally can't sleep very well on closed cell foam, so I carry a self inflating type mattress. I carry a 3/4 length, 1.0" thick pad to save weight, but a 3/4 length pad is only for 3 season use. A good 3/4 length 1.0" thick pad comes in at about 0.75 pounds. By comparison, the Cabelas short pad weighs 1.25 pounds.
If you're trying to get a pad that will be of year-round use, get a full length. A few years later, when you've saved up some money, you can get a 3/4 length pad to save weight for 3 season use.
I will also need a larger pack and maybe lighter tent before winter comes… as well as a warmer bag.
Lighter tent? For winter, tents are generally heavier although you may be able to find something lighter since your current tent is from Cabelas.
Suggestions welcome. We intend to camp thru the colder months if the boys are into it. I used to camp in 0 degree weather when I was a kid.
Good luck and have fun!