Well Bradsdub, it looks to me like you are making it complex yourself.
Choose one SurfSUP and one touring SUP. Enjoy them, paddle as much as you can and don't put pressure on yourself.
Surfing and SUPping is about fun, lifestyle and communing with the ocean and friends.
Please note this is my opinion only and if you feel the need to compete or have everything on offer you won't agree with me.
However I have been a surfer, paddler and SUPper for a bloody long time and this philosophy works for me.
Have fun.
ET.