Do they have the same warrantee? Do they both have solid tires that will not get flats? Do they both have slip clutches?
I have Landpride. I think that there isn't going to be much difference between the different brands for the same size cutter, with the same HP ratings. The extra weight makes me think the Woods is going to be stronger, but I don't know how important that is with a finish mower.
Landpride is super easy to get parts for. Their website has diagrams for all their mowers, so you can look up what you need, and order it online. I use Messicks, they are fast, their prices are good, and I never have to leave my house. You can also go to any Kubota Dealer for Landpride parts, but they order them too, so there really isn't any advantage to going to a Dealer to buy parts unless you want them to do the work for you. The one time I went to Kubota to buy a part that I assumed they would have in stock, it was priced almost double what I ended up paying for it from Messicks.
Woods is such a big name, I'm gonna guess that getting parts shouldn't be an issue. But since you have a Massey, you already know that some Brands make it very hard to get parts online. That's the one thing that I don't like about my Massey. I can only get parts through the Dealer.