Quick tips for getting into systems programming
What follows are a few quick-and-general pointers on "I want to start doing lower level stuff, but need a motivating direction for a starter project." They're somewhat un-tested because I haven't mentored any apps-to-systems transitions, but, as somebody who plays on both sides of that fence, I think they all sound pretty fun.
A word of warning: systems programming may feel crude at first compared to the managed languages and application-level design you're used to. However, even among experts, the prevalence of footguns motivates simple designs and APIs, which can be a beautiful thing. As a heuristic, when starting out, just code it the simple, ungeneralized way. If you're doing something interesting, hard problems are likely to present themselves anyhow!
Check out sites like hackaday.com to see the incredible feats that people accomplish through microcontrollers and hobby time. When starting out, it's great to get the tactile feedback of lighting up a bright blue LED or successfully sending that first UDP packet to your desktop at four in the morning.
Microcontroller-based development is also nice because you can build up your understanding of C code, if you're feeling rusty, from basic usage — say, keeping everything you need to store as a global variable or array — to fancier techniques as you improve and gain experience with what works well.
Although I haven't played with them specifically, I understand that Arduino boards are all the rage these days — there are great tutorials and support communities out on the web that love to help newbies get started with microcontrollers. AVR freaks was around even when I was programming on my STK500. I would recommend reading some forums to figure out which board looks right for you and your intended projects.
At school, people really took to Bruce Land's microcontroller class, because you can't help but feel the fiero as you work towards more and more ambitious project goals. Since that class is still being taught, look to the exercises and projects (link above) as good examples of what's possible with bright students and four credits worth of time. [*]
Start fixing bugs on low-level open source projects
Many open source projects love to see willing new contributors. Especially check out projects a) that are known for having good/friendly mentoring and b) that you think are cool (which will help you stay motivated).
I know one amazing person I worked with at Mozilla got into the project by taking his time to figure out how to properly patch some open bugs. If you take that route, either compare your patch to what the project member has already posted, or request that somebody give you feedback on your patch. This is another good way to pick up mentor-like connections.
Check out open courseware for conceptual background
I personally love the rapid evolution of open courseware we're seeing. If you're feeling confident, pick a random low-level thing you've heard-of-but-never-quite-understood, type it into a search engine, and do a deep dive on a lecture or series. If you want a more structured approach, a simple search for systems programming open courseware has quite educational looking results.
General specifics: OSes and reversing
If you're really into OSes, I think you should just dive in and try writing a little kernel on top of your hardware of choice in qemu (a hardware emulator). Quick searches turn up some seemingly excellent tutorials on writing simple OS kernels on qemu, and writing simple OSes for microcontrollers is often a student project topic in courses like the one I mention above. [†]
With some confidence, patience, maybe a programming guide, and recall of some low-level background from school, I think this should be doable. Some research will be required on effective methods of debugging, though — that's always the trick with bare metal coding.
Or, for something less audacious sounding: build your own Linux kernel with some modifications to figure out what's going on. There are plenty of guides on how to do this for your Linux distribution of choice, and you can learn a great deal just by fiddling around with code paths and using printk. Try doing something on the system (in userspace) that's simple to isolate in the kernel source using grep — like mmapping /dev/mem or accessing an entry in /proc — to figure out how it works, and leave no stone unturned.
I recommend taking copious notes, because I find that's the best way to trace out any complex system. Taking notes makes it easy to refer back to previous realizations and backtrack at will.
Read everything that interests you on Linux Kernel Newbies, and subscribe to kernel changelog summaries. Attempt to understand things that interest you in the source tree's /Documentation. Write a really simple Linux Kernel Module. Then, refer to freely available texts for help in making it do progressively more interesting things. Another favorite read of mine was Understanding the Linux Kernel, if you have a hobby budget or a local library that carries it.
This I know less about — pretty much everybody I know that has done significant reversing is an IDA wizard, and I, at this point, am not. They are also typically Win32 experts, which I am not. Understanding obfuscated assembly is probably a lot easier with powerful and scriptable tools of that sort, which ideally also have a good understanding of the OS. [‡]
However, one of the things that struck me when I was doing background research for attack mitigation patches was how great the security community was at sharing information through papers, blog entries, and proof of concept code. Also, I found that there are a good number of videos online where security researchers share their insights and methods in the exploit analysis process. Video searches may turn up useful conference proceedings, or it may be more effective to work from the other direction: find conferences that deal with your topic of interest, and see which of those offer video recordings.
During my research on security-related things, a blog entry by Chris Rohlf caused Practical Malware Analysis to end up on my wishlist as an introductory text. Seems to have good reviews all around. Something else to check out on a trip to the library or online forums, perhaps.
At the end of the page somebody notes: "This page is transmitted using 100% recycled electrons." ;-)
Also, don't pass up a chance to browse through the qemu source. Want to know how to emulate a bunch of different hardware efficiently? Use the source, Luke! (Hint: it's a JIT. :-)
One other neat thing we occassionally used for debugging at Mozilla was a VMWare-based time-traveling virtual machine instance. It sounded like they were deprecating it a few years back, so I'm not sure the status of it, but if it's still around it would literally allow you to play programs backwards!