My first tarp was the Hennessy napkin tarp. Talk about intimidating to someone that hadn't messed with tarps in more than a few years! I was absolutely positive that I was going to get wet using it; zero doubt in my mind. Luckily, I lived in Florida at the time, so all I had to do was wait a few hours for the next rainstorm. Every time I heard the rain, I was running outside with my stuff to practice. Within a couple of months, I was totally comfortable under that tiny thing.
My second tarp was an early SuperFly. It felt like a condo by comparison and I developed a bit of a crush on the big tarps. My time learning real tarp skills was priceless, but that SuperFly made things soooooo easy. Still, I learned this very thing while dragging my SuperFly along the AT:
Originally Posted by SGT Rock
I like a smaller tarp so I can have a tighter camp in cubbyholes.
There are so many more spots to hang when you have a small tarp, that it makes them very attractive. I had a OES Standard sent to me on the trail and instantly realized that I had no need for a large tarp unless I was dealing with cold temps. At least, as a thru-hiker on the AT. If it was raining and I wanted to cook under my tarp, I just took one end of the hammock down and I had plenty of room.
Since those days, my tarp purchases have been fairly balanced. I've got big tarps to use for blocking cold wind and entertaining camping friends and neighbors. Then I've got my 'hiking tarps', which are minimalist in size. They work just fine and if I had to, would work in winter too. I just wouldn't be quite as comfortable as easily.
So yeah, preference is the name of the game. In the summer, when I'm solo, I don't generally take more than my OES Micro. It covers every hammock I own and other than a couple of stupid-moments on my part, my quilts haven't gotten wet. My opinion, is to start small and learn by trial and punishment. Once you can use a small tarp effectively, making the transition to the big boys is nothing but pleasurable. Going the other direction might not be quite as enjoyable because you will probably feel like you're missing something.