going about this
Which part? How to generate the pdf files, or how to set up access control? The one thing I can say for 100% rock-solid certain is that HTML alone is not the way to do it. (This is the HTML subforum.)
Who are your members? Chess players, barbershop quartets, jockeys? n/m, not directly relevant, but what
is relevant is
#1 whether your members will normally be accessing the site from their own computers (meaning that information could potentially be stored in secure cookies), or might they be logging in from anywhere?
#2 how many members you anticipate having in the future. With a ceiling of 150 you can do a fair amount by hand, but if you're looking at growing into thousands of accounts you'll need to get more automated.
Do you prefer a server-side solution (htpasswd, or IIS equivalent, where some parts of the site are unconditionally off limits) or something at the user's end involving typing in a username and password?
How secure does it need to be? It's one thing to restrict access to chess ratings; it's quite another to restrict access to a bank account.