This quote confuses me. Are you definitely committed to going on a bunch of camping trips or are you considering bailing if you don’t enjoy the great outdoors? Because before I’d sink $500 into a hobby, I’d definitely test drive it to see if it’s something I enjoyed.
So my advice is to buy neither at this point, but to borrow a tent and a sleeping bag from a friend, if at all possible. Then, if after the first time, it’s something you’re incredibly stoked about, then consider investing in your own equipment. The great thing about waiting a bit is that you can investigate other people’s tents on your first outing. Crawl in them. See how easy they are to erect and take down. If it rains, make notes about which tent let in the least amount of water.
If you simpy must purchase one before your first trip, then I’d go to an outdoors store and physically crawl into the different tents. If you’ll be camping in extremely hot weather (highly unlikely given that you’re from WI), then you’d look for big screened windows that will let a breeze in. If you’ll more likely camp in cold weather, then a decent rain cover is essential, as well as a tent that can handle and repel high winds. Also consider that generally speaking, the more square footage the tent has, the colder it will be. Those huge tents with three different rooms are great for family camping in the summer, but pretty darn cold on a frosty October evening. Be sure to test the zippers!. You want zippers that don’t snag and that zip closed every single time. Because once the zippers gone, there goes your rain protection and there goes your mosquito protection.
There are some decent quality medium priced tents out there that are fine for the casual camper. Our 2-man Coleman tent has lasted for 15 years. I wouldn’t take it to hike Mt. Everest, but it’s fine for the type of camping we do.
Good luck on your camping trips. I wish I could go more often. Nothing’s better than sleeping out in a tent on a (somewhat) cold night, with just your nose sticking out of the sleeping bag.