I soldered only one SSOP so far - 20-pin CS4390. I used the
"bridge them all, then clean up" technique. I've never done it
before, and I used plain Weller conical tip (probably over 1mm)
on a plain Weller 25W iron. It took me about 10 minutes to solder it, then some more time to check connections with multimeter. It was a professional 2 layer board though.
When I was soldering much bigger CS4396 (SOIC), it took me
much more time on hand-made board. I haven't paid
enough attention and I had quite a lot of vias around and even
under the chip, and all their copper rings were tiny and
usually broken in half by drilling. I had tons of problems as the
area was congested and I had to solder each pin on its own.
My second prototype is hand-optimized to have as few vias as possible (remember, when you do board yourself, you must make via connections yourself, nobody is going to solder-plate the holes for you!).