I would start off by trying overnight primitive camping in National Forests coupled with dayhikes. That way you can start off using your car camping equipment, but won't be relying ion car camping amenities, and can slowly build up your backpacking gear as you become more comfortable in the wilderness.

Also, you really cannot spend too much on hiking boots. Also make sure they fit like a glove. Make sure you get little or no heel lift when walking uphill (most decent outfitting stores will have a ramp you can walk up and down), and while you want your boots snug, you want to make sure that your toes wont touch the front when going downhill, and that the width of the toebox fits. Most people wear their sneakers or everyday shoes a half or even full size big in my experience, especially men, so you may have to go a half size or even full size lower than what your sneakers are, but YMMV. Unlike sneakers, which all are built on very similar lasts (foot molds), hiking boots are all built on very different lasts by brand and often by model, so some brands/models will fit your foot's shape, others wont. Ones that seem to fit most people well are the Vasque Breeze GTX and Oboz Sawtooth Mid. Go to a store in person, and get the most knowledgeable person they have in their shoe department. Brands like Vasque, Oboz, La Sportiva, Asolo, HanWag, Scarpa, Treksta, Salewa are all good brands, but each show will fit differently, so try them on. Salomon is good if you're doing ultralight backpacking or day hikes, but even their best boot, the Quest 4D GTX, is lower quality and not as durable as other boots of the same price, but if it fits you or is on sale, go for it. Salomon's outsoles tend to wear out fast though, so be cognizant of that. Merrell, Keen and North Face are all lower quality for about the same prices, I don't recommend them. Especially the Merrell moab, which is basically just a sneaker dressed up like a hiking shoe. You should get a hiking boot with a stiff shank (support in the midsole) but a comfortable, flexible upper made of leather, synthetic or a combo. Also make sure that you get the right arch support foer you, whether it is built-in (as it is in Oboz and Treksta) or whether you have to buy superfeet or other molded insoles separately. Proper arch support (whether it is none or a lot depends on your foot) will help your feet not feel sore at the end of the day.