MacOS Classic
I recently bit the bullet and ponied up for one of those classic Blueberry iBooks (picture and entry in comp pending.) At work I'm a noted Mac hater after being forced to use it for several years while the company's Linux policy languished, but having now used OS 9 I can't help but feel like it's a better experience in theory than any modern OS. The interesting part is that it's hard for me to put my finger on why.I'll try to put my thoughts down as coherently as I can, plus the usual tips about running it these days.
But Why?
Like I said, it's hard to put my finger on what I like about the Classic OS. I think some of it comes from its limitations being kinda mindful: I find it to be a much better user experience for me to open a browser and be told "There's not enough memory to run this, close some programs" than to lock the system down with swap like happens on a UNIX or Windows.
I find its implementation of links (called aliases) to be better than the implementations elsewhere because they don't break. You can move the file wherever you want and it'll work. If you trash the file and try to use the link, it'll tell you that the file's in the trash so the link won't work (though it doesn't automatically delete it.) If I go to open a program and it's already open, I can see that because its icon is in an "opened" state. Oddly enough it reminds me of the Perl 6 motto: torture implementers to make users' lives as easy as possible. There's a philosophy and vision to classic MacOS that simply isn't present elsewhere.
Not only does it feel better thought out than its contemporaries or successors but also more personal. There are hotkeys everywhere, F7-F12 are reserved for your own use, it's incredibly easy and friendly to set default appearances. I don't need to find the magic directory for my applications: there's a folder for it in my hard drive. It's not special. I don't have to use it if I don't want to. Usually for commonly used apps I'll put them in there and alias them to the desktop. I made a Games folder for games rather than putting them in Applications. If I get too many more applications I might make some folders like "Development" to put them in, and all my desktop aliases will just work. It rules. It's damn near magical compared to the modern experience because the metaphors are both taken seriously and maintained.
Getting Set Up
In a pleasant surprise OS 9 actually comes with a decent amount of what you need. Since it's Apple you don't need any drivers, they already know your hardware. Unlike contemporary Windows you don't need to install a zipping tool or similar since OS 9 comes with Stuffit.
One thing you *will* want is a browser which works. OS9 comes with both Netscape and Internet Explorer. What you want is Classilla. Luckily for you Classilla is available over gopher and both of those browsers are versions old enough to support it! Go ahead and grab it here. Bear in mind that as nice and light a web browser as Classilla is, it's still a web browser. If you're low on RAM like my 128MB iBook don't expect much multitasking with it open. Enough for a text editor so you can write web pages, though ;).
Bonus: Classilla is also a fine e-mail client which will work with your current service, probably. It works for AOL at least. With your browser working, Gopher should be totally fine. As for the web Google will still work for you but you might also want to take advantage of FrogFind, a search engine by the Action Retro youtube channel for retro computers. It preprocesses linked pages, strips https, and should generally make pages that exepect 100x the ram work for you. Aside from that go ahead and bookmark The Macintosh Repository, who will let you in without https when it detects that you're on classic hardware. That's your main source of software.
For the most part you'll be able to find the software you'll need on Macintosh Repository. Just look for what you need and wander, that's half the fun of computing like this. The only notable exception I've found is if you're a weirdo like me who likes BBSing: the gold standard ansi terminal on Classic MacOS is Black Night, but you don't want the normal distribution. Head over to Captain's Quarters and grab his preconfigured, set up Black Night. It'll make your life easier. If you're gonna BBS anyway you might as well pop into CQII and thank Byte Knight for the help anyway. Tons of old mac users are there who know way better than me.