Miles,
To answer your original question, I think you could definitely go down to 40 degrees fahrenheit wearing everything that you mentioned while stationary in camp. You could maybe go down to 30 degrees fahrenheit, but only if you are an absolute metabolic hot house of a guy.
I use a somewhat similar system while backpacking in the summer. From my skin out it goes: Patagonia Capilene 2 Crew > Patagonia R2 Jacket > Marmot Trail Wind Hoody. This system keeps me warm to 40 degrees fahrenheit with no problem. I wouldn't be too comfortable depending on it to keep me warm with much lower temperatures than that. I mean, I wouldn't immediately freeze if it was 30 degrees fahrenheit out, but I wouldn't be very warm either.
I'll tell you what though, the ticket to extending the warmth of all these items is to include a warm hat and a warm gloves to your system. I think many people disregard hand (and to a lesser extent, head) warmth, especially on summer trips. I find that just wearing some simple gloves and a hat will drastically improve the warmth of my system, so don't discount these very light but effective items in your insulation strategy (you probably don't, but I thought I'd mention it anyway).
I find that each one of these insulative items mentioned above can be useful during the day if it starts to get cold while I'm on the move. I have worn items listed above in every conceivable combination, and each one has it's uses. You definitely loose that versatility when you only bring a very warm puffy (though, it's definitely warmer in camp, no doubt about that).
Also, for what it's worth, I find R2 and R1 fabric fairly similar in terms of warmth when used alone. The R2 is less resistant to wind chilling effects when used as an outer layer, but the it's also substantially warmer than the R1 when layered under a shell.
If I was going out for a run, I'd wear the R1, but I find an R2 to be a better layering item, so I usually take that when backpacking.
Hope this was helpful. For what it's worth, I'm totally with you on the advantages of fleece when it comes to breathability and ease of washing. I'm the type of person who likes to wash all my clothing items after a backpacking trip, and I imagine that I'd degrade a synthetic puffy pretty quickly with this behavior, so I stick mainly to fleece, even though I pay the price a bit in bulk and weight.