Well, right up my alley.
A lot of my gear is dual purpose from kyacking/canoes and backpacking, so I have some pretty light expensive gear. If you've got a 500lb capacity, you probably don't have to worry as much about weight. I like to keep stuff light for when I'm carrying it on my back.
After years on the ground I switched to hammocks a few years ago. I can say it definitely gives me a better nights sleep then laying on the ground. Anyone going that route you'll need a decent hammock probably 10ft if you're over 5'9" or so and top and bottom quilts. I prefer synthetic for on the water over down filled gear, because if it gets wet in an emergency synthetic can still give you warmth, where down us useless. Bug netting is a must along the water too or mosquitoes will eat you alive. I can give you some better ideas if you want to try that route.
Tents are going to be easier if that's what you're used to. Weight isn't as much an issue, as volume is. I like a 2 person tent for just me, but I take a 4 person if the whole family is going. I'd avoid most of the crap tents at Walmart if there's any chance of rain at all. I've yet to see one not get water inside in even a moderate storm.
Either tent or hammock and tarp, plan on 100-150 bucks for something that will actually keep you dry overnight.
Quilts or sleeping bag, look for something that will pack down small. Same as the tent. I like to fit my sleeping gear in a 20 litre dry sack, so it stays dry even if you roll it. This might be important to you TS from the stories I've heard.
Food, kinda depends on how indepth you want to get with cooking. Personally, I eat a lot of dehydrated stuff if I'm by myself. It's easy and you just need to be able to boil water to cook it. If I'm going with a group, we'll bring burgers or steaks or etc and do them on a camping grill. I have an older Coleman two burner for this, but there's others out there or you can always bring a great and cook over a fire. I always bring a small backpacking stove for coffee at least though. I like the BRS 3000t. It's super small works for boiling water. Remember, coolers take up a ton of space and weight, so the smaller you can get away with the better.
Other musts for me:
Water filter; I use the swayer squeeze. Filtering water as you need it is way easier than carrying it all for a trip.
Camp shoes;. Something other than the wet shoes I have in the kyack all day.
Camping chair: way better on my old backside than sitting on a log.
Some kind of pack, if there's any portaging possible. I hate making multiple trips back and fourth to the boat to carry gear. Doesn't need to be expensive.
For an example this is a pretty good tent for the cost:
Zion 1P, 2P and 3P Backpacking Tent
They have a pretty decent sleeping pad too:
ReCharge S Insulated Sleeping Pad
Here's another decent budget tent:
Amazon.com
And a cheaper pad:
Amazon.com
There's others out there, but those I've seen good reviews on. I have and have used that pad before too and it's not the greatest, but beats the hell outta laying on the ground.