I believe that the PIC family (prior to MIPS) has the most painful instruction set for everyone, which means that assembler is the preferred language if you want to save space, get performance, have control, etc.
The 8051 is a little less painful, more registers, but still takes a few instructions to do something useful (this means that you cannot compare them with other chips in terms of MHz). I like AVR in many ways, they cover the homebrew and developer community, or, if not directly, there is a much better family of developers there compared to competitors. I don’t like the instruction set, but decades ahead of PIC and 8051. I really like the MSP430 instruction set, this is one of the best instruction sets for assembly, TI is not so friendly to developers, it can be a struggle. The EZ430 was on the right track, but goodfet is better because you have no way to work with any other version of the kernel.
MSP430 and ARM have the best instruction sets, as far as I know, which leads to good assembler and good compilation tools. You can find commercial tools for all of the above and, of course, for free tools 8051, MSP430 and ARM (MSP430 and ARM can use GCC, 8051 can not, look for SDCC ). At the moment, mspgcc4.sf.net and CodeSourcery are the place for GCC-based tools for MSP430 and ARM. LLVM supports both, I was able to get LLVM 27 to beat the last GCC in the dhrystone test , but this is one of the tests, LLVM tracks performance, but improves.
Regarding the search and creation of free cross-compilers, I see that LLVM is already the easiest to get and use and move forward, I hope it will only improve. Unfortunately, the MSP430 port for LLVM looked like I could have done in a PowerPoint daytime presentation, rather than a serious port.
My answer is that it depends on what you are doing, and I recommend that you try everything. These days, grading boards are in the range below $ 50, and some are in the range below $ 30. Even within the ARM family ( ST , Atmel, Stellaris, LPC, etc.), there is a wide range of features and quirks that you will only find if you try them. Avoid primer LPCexpresso, mbed2 and STM32. Avoid LPC at all and avoid Cortex-M3 altogether until you cut your teeth on the ARM7. Take a look at SparkFun for Olimex and other boards. Although it's probably the LPC ARMmite PRO and Arduino Pro are a good choice. The EZ430 is a good launch of the MSP430, and I don’t remember who makes the 8051 stuff, the Renasys (sp?), 8051s are not all created equal, the register space changes from one to the other, and you need to prepare for this. I would probably be looking for the 8051 simulator if you want to play with the 8051.
I see AVT and, of course, ARM continues to dominate, I would like to see that the MSP430 is used for things other than ultra-low power. With ARM, AVR and MSP430, you can use and use the GCC tools now and in the future, which has many advantages, even if GCC is not the best compiler in the world, it is certainly the best supported compiler. I would avoid proprietary compilers and tools. I would look for devices that have non-proprietary software interfaces, JTAG is good, but for example, the new JTAG SWD on Cortex-M3 is bad. TI MSP was hurt by this, but some hacks have resolved this, at least for now. I'm really not very good at talking about PIC and I will not try. The big thing to look for is the glue logic, does a part or family have an SPI or I2C or any other bus you want to use, do you need an internal pull-up or wiring or input?
Some chips simply do not have this option, and you need to add external equipment. Do you need interruption with air conditioning? ARM tends to win this because it is the core used by many, so each ARM vendor puts its own I / O there, so you can still live in the ARM world and have many options, AVR and MSP will be very limited comparison. With ARM tools up to date, ARM is the most used processor right now. AVR and MSP are special project add-ons, less widely supported and fragile. Although ARM has low power compared to Intel on SBC or on a computer platform, it is most likely not as small as AVR or MSP. You really need to look at your project and choose the right processor for the job, I would not and would not limit myself to one family. With the same cheap price as scoreboards, and almost everyone can use free tools, it’s just a matter of putting in a few nights or weekends to get to know everyone. I suggest exploring more than one AVR and exploring more than one microprocessor.