I've met with my local shirt guy who does heat transfers and embroidery. We messed around today embroidering the logo on shirt material and finally got it right. Also had a cap embroidered that turned out really nice. I'll be getting him the artwork to have the transfer template made for doing T-shirts.
The logo is done and I've got a good local supplier to work with for these items. I plan to start out simple and basic and see how it goes from there. I also am going to favor quality products over the cheap stuff.