A leaky deck is a huge red flag, because it might involve balsa coring, rotten knees or rotted stringers if it's frozen and thawed in the bottom of the boat for a few years.
These things can be remedied, but it takes commitment, expertise and some skill. Also, might as well shave your head, because epoxy with stick in your hair otherwise.
Anyway, let's assume by some miracle the boat passes survey. Lots of boats do. So what? What is more important (particularly given that boats are coming down in price) is what you intend to do with it (daysail, coastal cruising, gunkholing, club racing) and how (do you intend on spending many nights aboard? Do you intend to do longer passages?)
Just as the type of software you use should dictate your choice of computer and operating system (most people are GROSSLY "overpowered" for browsing, mail and word processing), so should the type of sailing lifestyle dictate your boat choice.
A Pearson 36 is about as middle of the road a chunk of classic plastic as I can imagine. Next to 1980s Catalinas, it's about as close to average in all respects as I can imagine. It's not a racer, but it's not a slug. It's not roomy, nor is it cramped. You get the picture.
On the other hand, it is unlikely to surprise you with bad habits, nor will casual weekends on it be anything but a hoot, as it is well equipped, as are the vast majority of production boats, for coastal hops.
So decide if you want that...and if you do, that's great. Because trying to turn it into an ocean crosser, a racer or a liveaboard would lead to a lot of frustration. That's not what boats of this type were designed to do. They were designed to be messed about in.