313KB for one quarter of the UK seems way too small for me. I bet those numbers are wrong 
The chopping up has nothing to do with Mkgmap not scaling, it’s just that maptiles cannot be larger then 32MB afaik. Garmin itself does splitting of maps into chunks as well.
Regarding the commandline: We don’t live in the DOS era anymore. Linux takes up to 32k of characters on the commandline and Windows NT+ should be fine too. I suggest you make a script containing all the commands needed to create the images so you only have to build the Osmosis commandline just once. That way it doesn’t matter if it’s difficult to read or not.
It’s a wiki and you are the newbie who knows what’s missing there, so please add your ideas and tips so it helps other newbies too.
That’s indeed the idea of the gmapsupp option.
sendmap can combine images into a gmapsupp file and send it to the GPS immediately. It’s just that you don’t have to put the gmapsupp file on the GPS by hand if you use sendmap.
No, I have not heard of any such problem. But putting the SD card into a cardreader helps speeding the filetransfer (especially if the files are big), but could shorten your SD card life because of possible frequent ESD (electrostatic discharge). But I wouldn’t bother about both…