From the other side.
When you set up races you have the choice as to who pays the RW fee - the runner, the organiser, or split it 50/50.
After having set up the race details in RW diary, its quite easy to add the online entry.
In the past we have sent out numbers in the normal way. For the last two races we have said collect number on the day, and the race instructions will arrive by email.
This has actually caused more problems recently. Lots of people can't enter their email address properly, and unlike postal addresses there is NO redundancy in the spelling. get one letter wrong and it just doesn't deliver! Further our website hosting co also have changed their t&c so I can't bulk email all entrants from our hosted website address, so I have had to open a googlemail account to send out race details. These can't be a PDF attachment as its too big, so it went in formatted text. Hmmmmm. Grrrrrrr. Anyway, people seem to have got it now... except those whose email didn't bounce, but didn't arrive in the right place either...
On the up side, yes, Names etc are easier to read. For the organiser its a mixed blessing. On the up side lots of people seem to enter. On the downside, its more work and I'm not sure whether more postal entries turn up on the day compared to onliners or not. I think it would be an interesting hypothesis to investigate...
WE don't do our own online version yet, as processing costs are still there - it would be about 50p per entry on a normal race - and then if you want a super-whizzy swanky system you can expect to pay about £50 more per year for hosting - i.e. your own SSL/TLS certificate and a static IP address... There are other companies who will sort out online entry for you for cheaper... Not sure how well they work, but we'll see in the future perhaps...