scarrier is right on the money with regards to signal integrity, you really need to think about the ground plane implications on 2 layer boards. That said there are times when you need dual loading on 2 layer boards, just don't expect to fill the whole bottom layer with parts.
I do most of my SMT work under a stereo microscope as my eyesight isn't really good enough for 0.5mm pitch work without it. The only thing I would suggest is that you look on ebay for some pcb holders. They are sold for mobile phone repair, and clamp the pcb from the edges, that lets you hold the board flat when you have parts on the back side.
as for 2, I would always do high pin density parts first, as for them having as much clearance as possible makes the job easier. I tend to leave anything plastic till as late as possible (mainly connectors), so there is less chance of clipping one with the iron and marking it.
If you have a good iron set to the right temperature, you really shouldn't be damaging boards. If you are lifting pads regularly, then you need to sort your technique out.