I know I'm still pretty new to this forum, but I'd like to give my 2 cents if that's ok. I have a graphic design degree so I have to try to overcome problems with layouts/designs all of the time whether on business cards, tshirts, logos, signs, and whatever else. I think the 1st question that should be asked is this:
1: What are the goals of the tshirt? The goals, from my perspective, are to carry on the memory of a fellow buell rider, raise a little extra money for the family, and to have a shirt that anyone would want to wear, proudly(including people like me who never knew Arron, but feel a connection since I'm now part of this forum).
I believe the first 2 goals will be accomplished easily. The 3rd goal is what is holding everyone up. As mentioned before, how many times have you seen someone wearing a memorial shirt and not even payed attention to it. You most likely didn't know the person or the family so that shirt has no connection to you at all. My suggestion is to keep it simple. Have the D1 logo on the front and the quote on the back (straight lines of text across the back). Maybe have the years of his life on the sleeve. The "D" with the 1 in it on the front is very eye catching. The quote on the back is awesome as well. Having the years of his life on the sleeve would add to this commemorating shirt. That gives 3 opportunities for people to ask about the shirt. 1: What does that logo on the front of your shirt stand for? 2: That's an awesome quote, where'd you get that shirt? 3: What are the years on the sleeve for? Make the layout desirable so we still choose to wear this shirt instead of other shirts for months and years to come...the more/longer we wear the shirt, the more we accomplish that first goal of keeping that memory alive.
Another thing to remember....you're not going to be able to please everyone.