On the drills bits: PCB does dull HSS bits pretty darn fast Using a HSS will cause it to start getting dull by the time 10 or 20 holes have been drilled you will know the difference. and boy are those tiny bits hard to sharpen by hand 
I have been buying my carbide bits as resharpened and they do pretty good at a cost of about $1 each from http://drillcity.stores.yahoo.net/restool.html - and shipping won't eat you up either. I use an el cheapo drill press - $40 I think it was, and they sell for $50 to $70 now with a max speed of 3,000 rpm. I'm told you need at least 10K rpm, but 3K has worked ok for me todate. It is very easy to break a bit - especially those carbide bits really break easy - when trying to drill by hand. I have drilled several boards by hand using a dermel tool.
I was using the laser printer at work for my toner transfer, but finally broke down and spent the $75 shipped for a new P1006.
I have bent the pins on sockets many times for mounting like SMD also - not having to drill so many holes is one thing that helped me toward SMD stuff. I've been doing double sided boards for a while now. 90% of traces are on one side, with only a few that need to line up on other side - that helps because I don't get "perfect" line ups during toner transfer. I think it might be easier to etch two single sided boards, then glue them together - I did that once a long time ago, and I "think" it worked ok.
Have fun.
Ken H>