Rover Scout Tent 6'x8'

If you’re open to canvas, I’ll throw in a vote for the White Duck Rover tent! I took mine out this year and was honestly surprised at how solid it felt. I sat through a full rain and thunderstorm in it and everything stayed completely dry. I’m from Texas too! It's good in the heat but I've mainly used mine in the cold in Utah. The rover is small but feels like a little cabin, and the canvas actually breathes so it doesn’t turn into an oven the second the sun comes up. Setup is manageable on your own but once in a while just an extra set of hands to hold something is good too. It’s definitely more of an investment than the Magellan tents at Academy, but if you think you’ll be camping regularly with your son and want something that’s going to last more than a couple of seasons, the Rover has been a really solid upgrade for me!

Bell tents are the best for wind and storms. I like the White Duck brand but that's just my preference. I have their Rover Scout tent also and it has survived a few thunderstorms on Superior. It's lighter than the 13-foot bell I have. I love them both and rotate them every other trip. Neither one has leaked or had any wind damage from storms. Both are easy to set up in 15 minutes and, based on the few years using them, will be around for a long time.

Since you mentioned Kodiak Canvas, I’ll throw another canvas option out there. We’re a canvas tent and camping gear brand called White Duck Outdoors. Something like our Avalon or Regatta bell tents are nice for longer trips because you get way more living space and bell shaped tents handle wind and weather really well. We actually have people who refer to our tents as a second home since they can stay up for months (or years) without needing to be taken down so just what you're looking for with the "home" idea. With the budget you mentioned our two person Prota Springbar tent or our two person Rover Wall Cabin style tent would also be perfect and easy to set up and take down for a two person cross country journey! Some of our tents are at REI stores, however if you're strict with your budget, we do occasionally sell our Prota tents used exclusively on our website (usually from a photoshoot so only set up for pictures) for under $500. They’re not "instant" tents, but once you set them up two times, it gets pretty quick, especially if you’re mostly car camping. I would love to try and help with any questions, set-up ideas, or recommendations!

Mine is from white duck outdoors. They aren't cheap but quality usually isn't 

i'm really happy with the two White Duck tents I own. No frills, but sturdy and well built.