A Telemaster will require a real runway and more supporting equipment, pushing his investment over the $300 limit he's set. It's a nice plane no doubt, but it's more than the OP is looking to get into.

I'll second that the Apprentice is the best trainer out of the ones you've selected. I had recommended the Super Cub because you said you wanted a tail dragger. Jaka is right too. None of these planes fly themselves and they certainly don't land themselves. If you have a patch of tall grass to set them down in you'll probably make it through your first few learning flights without much trouble, but I would at least recommend getting someone with experience to do the first flight on whatever you buy to get the trims and throws set right. If you can manage joining a club, that's by far the best way to learn.