can i do this straight from boot and somehow emulate a keyboard?
Yes. Now, getting serial is a bit tricky - but it is fun and a good learning experience.
What I would do (If I was [sic] you), is buy another Pi. They're cheap and it never hurts to have more than one. Also, buy a serial level converter board (you'll have to figure this one out on your own) and get the serial connection working on the new Pi first. Basically, you connect one side of the level converter to 3 of the GPIO pins and the other side of it to your PC (generally via USB).
Once you have all the bugs worked out of the process, you can move it to the old Pi and it should "just work".
And some folks need to stop being fanboys and see the forest behind the trees.
(One of the best lines I've seen on this board lately)