I agree-I'm getting over my fear by jumping in. I just printed off 19 transfers yesterday and plan on finding shirts this weekend to iron them on next weekend. I plan on turning my house into a sweat shop and make all of my shirts, maganets, window clings, pressed penny tubes, candy bar wrappers, mousekeeping and spending money envelopes, stroller tags and just added to my list, pillow cases!
Don't get me wrong, it is a bit pricey to buy the transfers (I purchased my Avery ones at Staples for like $15 for a package of 5), t-shirts (depending on where you get them), ink for transfers (I've gotten 25 sheets of various things out of my cartridge so far and it's not starting to run out yet) plus the time you spend doing them (I'm setting aside a weekend-Friday and Saturday night-to complete the iron on part).
There's also an amazing thread about 20 steps to putting on the transfer that I'm using for guideance to complete my shirts and such. In the thread, there's even a link to a video to show you how to do it. The directions in the Avery transfers was not very clear at all-I was very thankful for the thread here!!
GOOD LUCK! It's really not as bad as it sounds! If you're worried about the shirts, start with something smaller, a pillowcase (if you want to practice fabric and such), or pick up some maganet or window cling paper and start there!