I’m sure you will get many responses to this post. Everyone will probably have varying degrees of perspectives on this topic. Personally, I would take along my own shelter even if hiking with someone else. I’ve met many people who start out together then one will get sick of hiking or for whatever reason will want to stop hiking. There are many lightweight options for solo shelters (i.e. Tarptent Virga, Henessey Hammock). Also, sometimes it’s just nice to not be crammed into close quarters for such a long period of time. There’s also the option of setting up your shelters next to each other as you see fit.
There are several sleeping bag manufactures who have great quality products (i.e. Western Mountaineering, Moonstone, Feathered Friends). Many people set small goals like getting to a certain mileage or a town. Many who set out with Katahdin or Springer in mind can burn out quickly. You can easily meet up with family, friends, etc. Once you’re hiking you will get into a natural groove and can estimate how many days it should take to the next town or road passing. Generally speaking you will be in a town or near one every 3-5 days. There are exceptions such as the 100 mile wilderness, etc.
I would highly suggest going as light as possible with gear weight within your budget. You can post your current gear list and ask for a critique. That’s one way of finding out what you really need. There are plenty of inexpensive things you can do to reduce pack weight like making a tin can stove, using 32 oz. Aqua Fina or Evian water bottles. Above all I would forget what you know about hiking and listen to those (and I don’t mean myself) who’ve hiked the trail.
guru