Hi Sqdancer!
Blue & Gold and Gran gave great advice! Just jump in! LOL.
As for writing or typing the letters... either or is fine.
Personally, I do type a letter that is general that I can print and send to each of my contacts. Many contacts share the letter with someone who needs mail, but as said before, some pass them around, post them on a bulletin board, leave them on the break room table, etc, etc... However, I do only send one letter to the contact regardless of how many are on his/her group.
HOWEVER, on the other hand, if someone responds to me from one of these letters, they then do get a more personalized letter in return. I have acquired several contacts in this way. For instance, Kim responded to a letter I sent to Scott who passed it along. Kim now gets her own letter, her own care package, etc.
It is really hard to do this WRONG! LOL.
Some people do pick smaller groups of say four and then send each of the four something... and that's ok.
At certainly holidays like Christmas, I do try to send each one of the group a stocking... for valentines day, they each got a card and a goody bag of candy... and so on, but let's face it, if my contact has listed a huge group of 50, 100, or more, I can't send each one something... but that is ok too!
One thing is for sure, you need to decide how much time and how much money you can use for this project... and then try very hard to stick to it. It is ADDICTIVE! You will want to do more and more and more!
Fortunately for me AND the troops, I'm in a position where lots of people are donating the items to me that goes into the boxes. I also have access to inexpensive auctions for pallets of items such as coffee, cookies, etc. So it really stretches my budget. On top of that, I have some great supporters who have helped with postage from time to time.
As an individual doing this, you may want to mention it to your fellow square dancers and see if there's anyone who wants to contribute -- a letter, a card, or postage... You may be surprised how quickly people are willing to do a little or a lot.
Some of my donators started out with a couple boxes of kool-aid and moved on to a case of it! Some started with a dollar or two here and there and now give me $20/month and they apologize that it isn't more!!!
So, SQDANCE! GO FOR IT! You will find it is one of the best projects you've ever gotten into! Your heart will be warmed as much or more than the heart of the one receiving your items.
Take care and ENJOY!
Anna - Baltimore, MD