I learned on a tail-dragger and never had any problems. I also learned in windy conditions and crosswinds; never a problem with the tail-wheel plane.

However, if you have been convinced that tail-draggers are the hardest of the two to learn on, then the tail-dragger is exactly what you should use to learn with. Also, don't be afraid to challenge yourself and learn in conditions that others are afraid to fly in. If you always take the easiest route then you will end up like many panty-waists who spend more time repairing planes than flying them.

When the wind picks up I go airborne while others go running home to mommy. One reason they spend so much time with glue all over their hands is that they never learn to fly in different wind conditions. They fly only when it is calm, so if they're in the air when the wind starts to blow they panic and begin looking for someone to come save them. If there's no such person around they will most likely crash the plane. They can't fly worth a flip but they can damn sure fix a plane.

Don't worry about breaking a prop; props are cheap. This really isn't a concern anyway unless you're using a wooden prop, which you shouldn't be using in the first place. You will probably land hard a couple of times and the prop will hit the ground. All that will happen is the engine will stop, but the prop will be fine. This will happen whether you are flying a trike or a tail-dragger.

Go fly and remember; there is nothing to fear except fear itself... the IRS.