To be honest, if you're starting out or starting back, you could just buy 4 corn cob pipes and call it a day! They cost 5-10$ anf they are durable... Not the most classy look, but they do last a long time and take a beating....
As to briar pipes, it's a hard one. There are very good quality 40-65$ pipes that can be bought. Look for brands like Butz Choquin, Chacom, Ropp, Jeantet and Lacroix for french pipes. Look for GBD, BBB, Prince of Wales, Comoys and Guildhall for english pipes. Look for Stanwell, Georg Jensen for Danish pipes and Peterson for Irish pipes. Look for Kaywoodie, Carey Magic inch and Missouri Meerschaum for american pipes.Look for Blatter pipes for canadian pipes, and Savinelli and Brebbia for italian pipes. They are quality brand pipes from quality material, but obviously, there are qualities and exceptions in every brand.
I kinda wish you'd be able to work out something with Blatter and Blatter pipes, they offer quality pipes at very reasonable prices (45$-65$). They are located in Montreal.
You could try your hand at New Old stock pipes from auction sites. But be careful, you have to know your stuff. Some seller don't, and you have to know for them!
Feel free to ask if you have any questions...
Gianni