You can usually blow enough air into a Presta valve tube to get it into a tire. You just have to kind of bite the valve to hold it open as you blow.

IMO, one drop of chain lube per link is WAY WAY WAY too much. Different lubes behave differently, but most people apply way too much chain lube. Apply the lube to the inside surface (that is, the side that faces the cog teeth) and wipe not only to spread the lube evenly but to remove the excess. I think I usually use about 10 drops of Pedro's Go! for my whole chain. Maybe less.

And, while a work stand definitely comes in handy for some jobs, lubing the chain isn't one of them, unless you have a fixie. On a freewheel bike, you can distribute the lube just as easily by pedaling backwards.