Oh no doubt. He'll be handheld and play as safe as possible, but I'm rooting for the wealth factor to kick in. It's a very easy mistake to make if you're not aware of the system. For those that don't know, Rimworld calculates the danger level of raids by the total resources you have stored in your base. More wealth = bigger badder enemies. Even on low difficulty, if his wealth is jacked up beyond his defenses he can get caught by a mech ship or drop pod raid. Sanity spirals are less likely, but with how little attention he pays to things I wouldn't be surprised if he gets got by that either.
On the other hand, if a dent handholds him all the way through getting a ship and getting off world, that's bizarre in it's own right. If at any point support drops, it's going in the trash, so the only way he's going to do it is if said dent sits there and finances the whole damn playthrough.