Re: 1985 9.9 sears Gamefisher
$450 is WAY too much for a 9.9 Gamefisher. Is this a Force or Eska based outboard. Either way the parts are hard to find and some of then no longer available NLA.
I bought a 7.5 HP Gamefisher (Force) that looked brand new for $400 2 years ago,,, outboards were selling for a lot more back them, bad economy

Anywho, this thing hauls a** for a 7.5 HP and I really like it. It's a de-tuned 15HP Force, like the 9.9 you are looking at,,, just de-tuned more. Problem comes in when you need to find parts. You can find easy things like impellers and plugs, but a lot of other things are NLA.
Reeds? NLA took me hours of scouring the internet to find them.
Ignition module/coil, BIM? NLA, had to get a $150 aftermarket conversion kit to fix 1 bad $30 coil.
If this is an Eska based Gamefisher I would walk away, underpowered and hard to find parts for. I also had a 1970's 7.5HP Gamefisher (Eska) and it was a pig compared to the 1988 7.5HP Gamefisher (Force).
If you need to take it to a shop for repair I've heard most places won't touch an Eska or Force, another reason to stay away.