When Webhosting plans say "x visits monthly" what do they mean?

Are they only able to accommodate that amount of money on a monthly basis, or do they cut you off once you reach that limit?

Also, why is it measured on a monthly basis rather than by the number of people viewing your site at one time? Doesn’t that seem more relevant?

It’s an approximate figure for the number of visits they can manage. Some hosts will not let you continue if you reach that threshold.