suggestions and guidance

Unfortunately, with that kind of budget, you're pretty much tied to X10. You could probably accomplish that with their outdoor motion detectors and something that'll do some scripting for you.

Maybe even check out vcrib.com - I only read a little bit, but the idea of using the cheap X10 sensors seemed kinda handy... and using just RF you can probably make it reasonably reliable.

I'll be really curious how reliable those outdoor sensors are. I'd imagine you'd want something smart that requires motion on more than one of them within a set period of time before calling it motion, or that indoor chiming will probably be going off all day and night. If not, then I'm really curious why the outdoor wired motions sensors are over $150, and the X10 one is $20. That said, you'll want something that lets you do a little bit of scripting to add in some cheap additional reliability.
 
... hoping to get this basic stuff done for less than $300. Is this at all possible?

Yes. You can start with X10-based gear and see how that works for you. There are many products (new and used) available on eBay and on x10.com (have an air-sickness bag handy because their site is "an experience").
 
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