Thanks for all the feedback guys, I picked #2 as well, it looks like I'm in the majority. I tend to wait till I can hear my chain making a little noise, or I look at it and feel quilty
That seems to end being about every 500 miles or so. I'd love to keep it better lubed, but lubing after every ride or during rides isn't going to happen for me. I am going to look into the Belray synthetic lube suggestion, and check out the Scott-Oiler as well tho.
I'm also thinking it might be quicker and easier to just spray the chain lube into a rag, and wipe it on the chain good...would save the big hassle of overspray all over everything (a pain to clean off the bike/floor etc), and would be much quicker and easier than putting the bike up on the stand, or rolling and spraying. I might actually lube after every ride that way