"Would investing in something from the Heritage line fall into your first method of upgrading? "
I am kinda a step or two ahead of you in my journey. My love is Home Theater and I can tell you that La Scalas, of the Heritage line, are a great start. Used pairs can be had when you watch Craigslist and the Forum. I picked up a used pair for $1000. The sound quality and volume is absolutely impressive! Now, I upgraded from a pair of Sony SSF-5000s (currently my surrounds). I know my direction will be a complete Heritage 5.1 (hopefully even a 7.1 or 2...wishful thinking ) Home Theater. Yeah, my journey will take me a few years for sure, but I'm looking forward to the ride.
From my perspective, it's definitely better to save and get what's Right for you rather than what can be had Right Now. I've made my plug for Heritage. Whatever you decide, enjoy the ride, post pictures, and draw from the wealth of forum members here! Most are friendly enough to let you audition their gear too!