Really, the programmer is just the data cable. All programming of the chips is in circuit, it's just so easy and fast it's difficult to justify making up a socket programmer at all.
The development board is programmed through the debug interface on the board. You can reprogram / debug that chip as many times as you want without removing it. If you don't want the development board, and just wat the progamming cable, you can buy the cable seperately for $20.00 and it comes with the development environment. Updates to the IDE/compiler/assembler are available from the Zilog site with registration.
I wrote a little page on setting up the 40pin dip on a breadboard a long while ago. I need to update this page with the projects I've completed to date.
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I haven't bought a DIP chip in a long time, though. I mainly use SMD now. As an easy example you can see the simple little lightshow board I made up with a 4k 20pin chip. The first 4 pictures are the one I made for my computer with an I2C connection on it. The last 2 pictures is a simpler version that I'm putting in my sons halloween costume. WIth both of them, you can see the 3 pin header on the top of the board. That's the programming header. It's not a bootloader or anything like that. It's power, ground, and 1 wire debug/programming interface, with no other passives. It's fast. It's comparible to the load times you mentioned, 2 seconds for an 8k chip, 4 or 5 seconds for a 64k chip. It gives you full debug ability in C, breaks, watches, steps... One slightly annoying thing is that this one wire debug/programming pin can only be used as that. You can't reassign it as GPIO or anything else.
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Here's a fan controller, temp monitor I started on for my external PC watercooling project. The first few pictures. Same thing, I just have the 3 pin header on it for programming, debugging. Actually the last picture you can see the test breadboard setup I was using to try and figure out the final hardware design. The grey box with the beige cable in the back right of that last picture is actually the latest programming cable that ships with the kits.
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