This is an interesting topic. I often enter lotteries but if I win usually ask the host to send the card to someone I am running an NonRAS lottery for. I am selective about which lotteries I enter. As a participant I usually try and add a message with a bit of depth rather than “Thank you for the lottery. I like X”. I notice there are a lot of people that enter every lottery and don’t put a lot of thought into their messages. I think it is an effort for the host to run one and it is a shame when people treat it as a freebie rather than a opportunity to connect. Like you, I do not begrudge it if I do not win…it is simply the luck of the draw. I always check postal monitor before I enter.
I have only hosted two lotteries, one chain and one regular lottery. In both I did hope some of the more thoughtful participants with interesting answers won. I have an unusual lifestyle in that I housesit most of the time so I am on the move a lot. When participants request the card send in an envelope it is inconvenient as I don’t try to just keep essential items with me and I don’t have a supply of envelopes that fit postcards easily (a regular business envelope is usually too small). I think if I was offering future lotteries I would just add a rule that the postcard would be written and stamped. The first lottery I ran was a regular one and it generated a lot of interest and great conversation. I was pleased with how it went. The second lottery was a chain one and I didn’t get a great deal of interest, which was disappointing. It is a lot of work to keep up with the comments and to remember to close it, send cards etc. This is why I value people who write thoughtful messages. One of the terms of the chain lottery was that the winners hold a lottery themselves. So far two of my winners have not done this (to the best of my knowledge). In the future when holding a lottery I think I would state that I will post the winners cards when their lottery is up and running and I would note this in the initial post to launch the lottery to prevent this situation. It is a bit uncomfortable to have to send a reminder. I was more inclined to go the extra mile for winners who entered with a quality message i.e. one was a stamp collector so I used lots of vintage mint stamps with themes that fitted their profile wishlist.
I have appreciated it when winners have messaged to say they got the card and when they really value the card.
I don’t have a preference for being a participant or host but I find it fun when a lottery creates interesting conversation or when I learn something new.
A shout out to @DaisyDekker who often runs lotteries and she manages to get some great conversation going.