I cannot necessarily comment on all your requirements, but my favorite 8 bit environment for the last 10 years has been the Silabs IDE and their 8051 family.
They cover the whole gamut from a small 11 pin device to 144 pins monsters with excellent analog functions and fast processing (25MIPS minimum up to 100MIPs), the fastest 8051's I have seen.
The IDE is well done and solid. They support the usual suspects tool manufacturers including Keil and the free SDCC. The debugger works well and is non-intrusive. Most devices are programmed and debugged via 2 pins, one being the reset and the other that can be shared with normal functions when not debugging.
They all have a 25 MHz precision oscillator such that a crystal is usually not necessary. Those that run faster than that have a PLL.
The IDE is fully functional and fairly bug-free, but aside from solidity, not something to write home about.
All in all, a very functional package that is essentially free (if you use SDCC).
Silabs has set a very high standard with working tools and code examples that run out of the box with a minimum of fuss (that applies to their Cortex-M3 line as well), unlike many of the ARM wannabees these days.
Probably the only thing negative I can say is that they do not have any DIP packages, so not so great for hobbyists. However, many of their chips are available on a small development tool called the Toolstick. They have toolsticks for most of their chip families and they usually cost about $10, so for prototyping, they are ideal.