#2
1. Unfortunately I can't answer this question because this is your gear and it's up to you.

2. Don't know but ebay is generally a good place to look for used gear prices.

3. First 2, the latter 2 should be your final options as they will try to rip you off (even ebay to an extent). Also stuff like craigslist, and gumtree are always viable options. And to an extent check out musician forums and try and post on them but you must be cautious of rules for doing buying and selling and you should carry some sort of reference of a previous sale so they know you're legit.

4. Everyime I've sold shit together I've lowered the price as an incentive but really just do whatever maybe the Epi and MG and crybaby as some sort of beginners package and the squier as a beater or modders guitar.
#4
you'd probably be better off selling them seperate i would imagine. I tried to sell my squier strat they would only give me $100 for it and theres not a scratch on it so i wouldn't sell it at a pwan shop or guitar store i would do ebay,craigslist etc.
#5
Will you have an amp to play the tele through? You might regret selling the Crybaby aswell.