For the 2nd, i don't understand why you have to reboot the htpc when waking it up... if it was in suspend mode (look for power saving option in kodi settings), it will just....well wakes up ?
For the first, i just want to advertise that this solution is IMHO a litlle overkill for what you want to achieve. Editing remote.xml or even Lircmap.xml would be maybe easier.
Enven creating a Windows PC device under harmony and pair the remote via bluetooth would maybe works (the remote will be see as a keyboard, but i don't remmeber if the basic keys are available it the s***y harmony app).
The only way i think it would be usefull is if you use a keyboard in your htpc and are satisfied by the way it works and you don't want to bother to edit some xml files to mimic this to your remote.
Another important think too is : not all the keyboard keys will be mapable. I don't know why, and i searched a lot an explanation, but the way openelec/kodi works on that matter is absolutely cryptic.
Well my test showed that all the letters work, all the number, a lot of the basic keys like enter, backspace, some others too. But for example "home" works, but "end" will not be catched by Kodi even if the system send the correct mapping. Esc will not works too as all the F1, F2... keys. the .dot, the comma will works... I didn't tried them all so you will have to see for yourself.
Problem is right now is a little late here so it will have to wait for monday (can't do this tomorrow).
In the meantime what you can do is grab WinSCP and MobaXterm, install them and set them up.
What you could also do is check if all buttons of the remote actually send something by testing theme using these command :
Code:
Killall eventlircd
Ir-keytable -t
then press each of the remote button (ghort and long press) and see if scancodes are received for each button.
Ctrl-c to quit this and type reboot to reboot your box as your remote won't work anymore as you killed LIRC.
Have fun