Always ask.... when was its last rebuild? New bearings, rubber etc.
The high top is worth something, as is the wrap. But without knowing when the new bearings and seals and rubber and carb kits etc was last done... yikes.
no decomp, broken clutch cover, tweaked gas tank, missing operator presence lever, starter cover is buggard...etc. that saw is nice enough that is deserves a full on rebuild, but at minimum look at it in current cosmetic shape, then determine a value fully rebuilt. then determine what it'll take you to get it to that point. then its a math equation. Fully done up, ported, powder coated, new bearings, oem this and that, might be in the 1k range. just gotta figure out what $$ it'll take to get there and then you have a math problem to solve
the rough answer is to offer the guy probably way less than he wants.... its a project for sure.