I don't have a recommendation for a particular tent. However... I do have some advice on learning to set up a tent for those who don't already have experience.
A.) You will need to practice setting up your tent. Do you have someone with REAL experience with tents? If you know that Uncle Bob hasn't camped since he was a Boy Scout 40 years ago when he was 8, I wouldn't ask him. Find a friend who goes every summer. Once you find that Special Friend ;-) ask them if they would teach you at your home and offer to cook (or get carry-out) that night. Have them guide you through it (not show you) until you're comfortable doing by yourself with your child running around hollering at you. You're a Mom: That'll be the easy part! If you do it at home, then you'll be familiar with everything that is in your tent pack or find out if anything is missing and get it replaced. Also, practice repacking it into the tote/carry/storage bag IT CAME IN. Easier said than done. My first few times, the tent ended up just rolled up in the trunk and re-packed AFTER we came home :) and that was BEFORE kids!
B.) Is there a weekend program in your area that teaches camping: INCLUDING setting up a tent? I know you're in Oregon, but I'm in Texas so here is what we have down here:
The Texas State Parks Systems has The Outdoor Family Program for $55 per weekend. They even supply the tent! Here is the basic information on the website:
Texas Outdoor Family (TOF) workshops are hosted at state parks where your family receives hands-on experience learning basic outdoor skills. You will learn everything you need to create great memories enjoying the outdoors with your family, including:
•How to set up and break down camp (including your tent)
•How to use a GPS
•Introductions to a wide range of outdoor activities (such as fishing, kayaking, wildlife watching) depending on the site location, facilities and the season of the year
Best of all, no experience is necessary and you get all the help and advice you need from highly skilled outdoor specialists and trained volunteers!
Here is the FAQ link so you can ask your State Park Systems if they have something like it: http://beta-www.tpwd.state.tx.us/outdoor-learning/texas-o...