Need Help with PuTTY

I have built a serial-controlled device that works with putty...I can press a keyboard key, and putty sends it down the line to start a script on the device. Everything works fine, but not perfect.

I need to setup putty so that when I press a key, it will send a hex code (like 0x0A) down the serial line. Not only that, but when I release the key, it should send a different hex code (say 0x0b).

I would also like to be able to configure it so that if I press a key quickly and repeatedly (say 50MS between clicks), it just treats it like I held the key down the whole time...only sending the "release" command after the key has been released for however many MS I have set it for (50MS in this example). This is not as vital as the first part, but it is vital to achieving the perfection that I desire. If this functionality could be provided, I would only want it applied to a few keys.

I am not married to PuTTY...if there is some other app that will serve me better, then I'll switch...if there is some script or configuration option that will allow PuTTY to work like this, I'll use that.

Also, I would like to record the actual serial outputs in real time...to a file that looks something like the example below. I would then want to "play back" this file to repeat repetitive tasks.

example log file:

00:00:00:00.00 :: Communication Starts
00:00:00:10.56 :: 0x21
00:00:01:05:34 :: 0x22
...


[edit]
I have figured out a way of sending different keys for press and release through the use of autohotkey...I still need to figure out the click delay, but I think I can work around that.

That just leaves the recording/playback...and I'm sure someone has some idea on that?