In the first photo in the second set, sorry for duplicates, I didn't think the first set went through, where the t1-11 is painted brown and fern hanging above, there is a gap on the bottom and behind it there is an area that has a gutter around it. There is no drainage anywhere else on the deck. In the second picture, where you can see the garage roof, water sits there in some spots. Before we bought the house, they did repairs on the railing and put new t1-11 where it is primed. I believe this was due to rotted wood. In the corners where the tiles/grout meets the wood, there are thin gaps, so water could be coming in that way. I'm not sure why they would fix all the railings and leave the tiles as they are. So there is a problem with drainage due to the leveling of the deck. I was thinking of at least re-grouting the tiles, replacing the cracked ones, putting in some kind of sealant in the corners where it meets the wood and hopefully this would water proof for the time being. Again, I'm not sure what is under the tile.