Yeah.. but, you can do that. Go look at a Pro-mini, it's some fun soldering!
I'm sorry, but this should be in the Hardware selection. You might get more answers there.
I've never seen that error, you do have the right board selected right? And what do you mean by "Spamming the serial port?" Just printing to the Serial port one after another, without a delay?
That wouldn't lock it up, but I've never had the Flash error.. so I'm not really sure what to say! Have you tried Manually pushing reset when it's uploading?
Something else that took another member a while to find, it came up with the speed error, like you had the wrong board selected.. but turns out his Crystal or Resonator fell off, so it kept giving errors.
Just things to check for, good luck! (And move this to the Hardware selection!)