Agreed transitive. Regardless of game type. The first upgrade needs to be bought. In fortress, they are mandatory. In that mode the fortresses can be viewed as your health. Dont you want your health to regen?
I bought the first level. Don't the rest of them just give like +5 regen and +300 HP or something? They were utterly useless in beta, but maybe I missed a buff.
About the other demigods: the thing is, I can actually defend against them by, y'know, hunting them down and killing them, setting up observer wards and intercepting them before they reach the fortress, or scaring them away while the fortress regenerates. Oak can just ignore me and still wipe out my fortresses. This guy wasn't even doing it as well as he could have: he should have shielded himself on the way in to make sure he got there and did maximal damage before dying. I also don't think he had as many points in Shield as his level allowed -- that would make this even more effective.
Also, if you can't push better than a single suiciding player and all the money he's giving you. Something is wrong.
The problem was, we had to push the traditional way, where you don't, you know, die. That means we had to take out all the towers in front of and around the fortress first, and deal with defending demigods. He just ignored everything. I will admit that we had let some of our front defenses go, because we had trouble early on and because I didn't anticipate this strategy -- when it was 2 fortresses to 2, we were dominating the map to the point that we could defend fortresses easily, until he got Last Stand. I don't think it would have mattered. He would have ignored them the same way he ignored us when we jumped him on his way out of his base. (and if he'd been smarter, he would have approached the fortress with his shield up)
Anyway, I'll see if this happens next time I'm up against Oak, or if I was just dumb. I guess the smart money is on the second option there. 
Probably the best counter is to buy lots of structure health (except I still think that's useless...I'll have to look at the stats in-game), and to just concentrate on knocking down his fortresses. I think our biggest mistake was that we tried to defend; once your opponent does this you have no choice but to attack as fast as possible.