should i pay for any lost/missing articles myself?
No, insure the packages, or give people the option for an insured package, with the understanding that if they opt against insurance and something goes wrong, they're out of luck.
how many extra tshirts should i order each time? (once a run is done thats it, it is way way way to cost prohibitive to order less than 20 at a time so if i am out of replacements i really cant get more)
It depends on how great the demand will be for the shirts -- which might be hard to gauge. I would order a few extra. If the minimum is going to be 20, then get 24 or so. If I recall correctly, a lot of screenprinting companies declare that if they deliver 2% above or below the ordered price, the order is considered 'fulfilled'. That's so that if you encounter some issue and botch a print, or if the 'extra' shirts you print come out perfect, they're not wasted. When I used to print t-shirts in my business, that was my standard practice. So if you ordered a gross (144 shirts) I would throw in, say, 2 extra shirts when printing, in case something went wrong. I stipulated that the client would take 142 or 146 shirts, and pay for the extras if they came out alright.
I think you would eventually sell the extra shirts.
with the proto shirts, i literally have what was ordered, i have no extras anymore and this has gotten me in a slight panic, what i will say is this, i plan to not let that happen again, and with the june shirt i have ordered several extras in each size, hopefully i wont have an issue replacing anything after the prototype run but just really wanted to get a clear idea what public perception was on how i should treat/handle any issues that come up as this is a non profit deal and sometimes im running very close to the bone on costs, particularly when things like multiple colors/backprints are concenrned
Increase your prices -- don't run into the red on these. Also, limit the sizes -- perform a poll to see what the two most popular sizes are, and that's likely it. You don't want to get stuck with five of a size that isn't particularly popular.
i want to make sure i am offering the best service i can, and cut issues and my costs to a minimum, this does take up a reasonable amount of my time and i am totally happy to donate that, but i would really love this to be a monthly thing and i cant do that if i have to cover too many costs out of my own pocket
Someone suggested that this become a quarterly (seasonal) event. If monthly is too great a strain on your time, then yeah, I second that idea.
sorry if this all made little sense, just trying to put out a few concerns of mine and see what people think
I'm glad you said something! If you need help getting artwork or designs together, ask me for help, I'll do what I can. I did have one idea to perhaps spur sales and get you to your minimum order quantity. Let's say you've fully funded the t-shirt buy for that quarter when you get the first 24 shirts sold. Let's make a design element that the screen printer can leave in place for the first 24 shirts, but leave out for any additional shirts. It could be something small, and not immediately noticeable -- an asterisk or something, something that could be easily blocked out by the printer. The first 24 people to pay their invoices will have this small element retained, and the rest will not see it -- an incentive to pay quickly. Nothing drastic, more like an easter egg.
EDIT: Maybe one of the first 24 people to pay their invoice will get a single shirt with gold print -- like Willy Frickin' Wonka's Golden Ticket.