When I started, about 5 years ago, I had a cheapo, free-with-purchase 20ct humidor with five Rocky Patel Olde World Reserva Maduros in it, and now I have multiple wineadors.
I've often told people to go way bigger than necessary, but I've rethought that position. Here's why:
-Coolers are cheap. A 28qt is $20 on Amazon.com, and a 150qt goes on sale on Walmart.com regularly for $50. So you're not talking a lot of money to upgrade.
-The environment inside a coolidor is a lot easier to regulate when it's mostly full.
-Most important, you're just getting started. There's absolutely no reason to be tempted to grow a huge stash all at once, which buying a huge cooler will definitely do. Take your time, smoke a lot of singles, develop your palate and preferences. Your palate will change over the next couple years, and sticks you might think amazing now you may not even want to smoke in a couple years. Take it slow, wait to stock up until you're far enough along in the hobby to buy for flavor and preference, not for brand or bargain. One way to help yourself wait is to keep your extra space somewhat limited.
My recommendation for you right now is to grab a 28qt cooler, a few Boveda packs, and four cheaphumidor.com cigar trays (they're sometimes cheaper on eBay). That should suffice for a while, and when you out grow that, get another. When you outgrow both, grab a big cooler, and pass the little ones to guys new to the hobby, or sell 'em.