I think that depends on (1) whose perspective we're looking at this from, and (2) what the future holds for the combined company.
In terms of liquidity and it being "a sure thing", an acquihire would surely be better for Exec. But Justin Kan already has a few successful endeavors under his belt and probably isn't hurting for a quick check. Increasing his odds for a homerun probably makes more sense. The same probably goes for the investors.
For the employees on the other hand, an acquihire and subsequent retention package would most likely have a better EV/Risk ratio.
Home services is an enormous market and handybook looks well positioned to be a name brand in the space. I think you're correct that this is placing bets on a homerun.
In terms of liquidity and it being "a sure thing", an acquihire would surely be better for Exec. But Justin Kan already has a few successful endeavors under his belt and probably isn't hurting for a quick check. Increasing his odds for a homerun probably makes more sense. The same probably goes for the investors.
For the employees on the other hand, an acquihire and subsequent retention package would most likely have a better EV/Risk ratio.