Welcome, I hope you enjoy your stay.

My take on your questions:
1. No. If you aren't going to "have 50 cigars in my humidor" just pick up what you're gonna smoke.
2. Sure you could, but a zip-lock baggie and a water pillow would work better, imo.
3. Search the board for mild/medium smokes or smokes for beginners.....I'm sure you'll find something there.