Find some simple Python libraries to use, and going all Python is probably best. Combining Arc and Python would be a fun project but would distract you from getting version 1 done :-)
System administration is tedious but not very hard to learn. An advantage of doing it yourself is that when you need to do some minor tweak you can just do it and not interrupt your flow, instead of emailing some guy who does it the next day but it isn't quite right so now you've been stuck for two days and then he's had some important emergency so he can't get back to you right now... For help with system administrations issues you can ask questions over at http://serverfault.com/ if you get stuck on something.
Security is figuring out that you don't want people to be able to do X, Y, and Z and then making sure that they can't do X, Y, and Z. The simpler your system is, the easier it is for you to check. Which is another reason to avoid complicated software that you don't need.
For passwords specifically, for version 1 just do something very simple. Use OpenID if it won't confuse your users and you won't have to store passwords at all, or just collect the usual username/password and stick it in a simple file on your server. Then as you get going you can come back and take another look, but don't get hung up on it for now.
System administration is tedious but not very hard to learn. An advantage of doing it yourself is that when you need to do some minor tweak you can just do it and not interrupt your flow, instead of emailing some guy who does it the next day but it isn't quite right so now you've been stuck for two days and then he's had some important emergency so he can't get back to you right now... For help with system administrations issues you can ask questions over at http://serverfault.com/ if you get stuck on something.
Security is figuring out that you don't want people to be able to do X, Y, and Z and then making sure that they can't do X, Y, and Z. The simpler your system is, the easier it is for you to check. Which is another reason to avoid complicated software that you don't need.
For passwords specifically, for version 1 just do something very simple. Use OpenID if it won't confuse your users and you won't have to store passwords at all, or just collect the usual username/password and stick it in a simple file on your server. Then as you get going you can come back and take another look, but don't get hung up on it for now.
I'm "aw" on arglanguage.org, by the way.