If the basic grading around your how wasn't done correctly at the build or over the years has settled badly... the best option would be to get it graded again.... but this is also the most costly and destructive to any existing landscaping you have in place. Since no one else has jumped in… here’s my take. I am not a pro… so take that into consideration. But if I had a similar problem.. This is what I might do. Adding porous soil on top won’t help. This would include sand, many “topsoils” you can buy at big box stores, or most likely any “dirt” you can buy at a big box store. Many times these aremade from organic materials which will break down over time and you will end up in the same spot. They typically don’t have much mineral content which won’t degrade. Assuming you have clay soil… you would want to add more clay soil to match the clay soil below your top soil. The dense clay is what will direct your water in any directiong. So you could scrape back the decent top soil you have until you get to the subsoil and then add the new clay soil….. Increasing the slope. Then pull the decent top soil back. You could find a source for “clean fill dirt” or just find some cruddy clean dirt from construction site to get the “clay” that you need. Or you can get it delivered. It’s a lot of work. Another option would be to add a french drain of some sort. There’s many youtube videos on this process. It’s a lot of work too! You have any pictures to give a better idea of your issue?

I'm a little confused by your description, but why exactly aren't the weep holes working? Are they too small or is the floor not sloped towards them as it should be? If they're too small, then you should be able to enlarge them. If the floor is too flat, then you may well have to redo the floor to enable it to drain properly. You could also try and work something out with rain gutters around the perimeter of the roof there but it's probably not going to look great.

It doesn't matter if there is a 3" hole in the bottom of your pot, or a 1/4" hole. When the pot has been watered to beyond the point of saturation and left to drain, the amount of water in the soil is called 'container capacity. A battle between 1/4" and 3" would turn out to be a draw, same amount of water in the soil at container capacity. This also holds true for 1 hole vs 10 holes - same amount of water in the soil at container capacity. Also, if the soil supports perched water, the ht of the PWT in either case would be the same. The only real benefit to having more "hole space" is the pot drains a little faster, but the plant doesn't care if it takes 60 seconds or 6 minutes for the soil to drain. It does matter if the drain hole(s) is/are not in the bottom, though. That can be a serious problem. The bottom of any drain hole in the side of the pot should right on the bottom of the pot to avoid unhealthy issues. The ideal place for the drain hole(s) is through the pot bottom at the pot wall. That way, you can tip the pot with the hole at the lowest point. If you use water-retentive media, simply tipping your pots after a thorough watering will passively eliminate a LOT of excess water from the soil. See A vs B below.Also, take note of E - using a wick. The shaded area represents perched water. Drilling holes in pots Masonry bits work fairish for drilling soft clay terra cotta pots, but are not the best choice. The 2 types of drill bits most appropriate for drilling holes in pots are a diamond core drill for the highly vitrified (hard material - baked at very high temps - glass, ceramic, ......) pots, and a drill with several names for drilling clay pots fired at low temps, such as terra cotta. That (carbide) drill is called a 3-point drill, spear point drill, or a spade drill, seen here: For the hard stuff, diamond core drills are best, though the 3 point drill will drill the hard stuff, too. You can buy either type at big box stores. They're not that expensive, and they last a long time if you take care of them. They are best used with a steady stream of coolant from a squeeze bottle (contact lens solution bottles work great for this) or with the work surface barely submerged; that is to say, put the pot upside down in a tub and fill the tub with water until it just covers the work surface. If you use a spritzer or squirt bottle, a 50/50 mix of antifreeze and water is an excellent coolant, and soapy water is better than plain water but not as good as the antifreeze mix. The coolant keeps the tool from over-heating, and in doing so, increases the life of the tool substantially - like triple or quadruple the number of holes you can drill. As noted, regular masonry bits are "ok" for drilling terra cotta or cement (you can make them work), but inappropriate for anything harder. The right tool makes everything easier. Al

If there are that many broken places then you should replace it all. It's just a mater of time before the rest of it breaks. You might be able to abandon the old in place and just install new near it.