2-word chain:
playtime $\rightarrow$ timeout
3-word chain:
playable $\rightarrow$ ablest $\rightarrow$ stout
4-word chainschain:
playtime $\rightarrow$ timeout $\rightarrow$ outlay $\rightarrow$ layout
with spaces:
-
playtime $\rightarrow$ timetable $\rightarrow$ tabletop $\rightarrow$ top out (not sure if this last one is valid)
-
playboy $\rightarrow$ boyfriend $\rightarrow$ friendzone $\rightarrow$ zone out
5-word chain:
playoff $\rightarrow$ offbeat $\rightarrow$ beatable $\rightarrow$ ablest $\rightarrow$ stout