Looking at that picture if you're just going to add on making it wider I would add on to whats there. If you're going to go deeper I'd think about starting from scratch.
Use a steel bar to loosen up the dirt, then with a good strong shop vac **** up the material. Keep repeating this until you make it 3 -4' deep and this should take a lot more water into the ground.
Hard to tell from your pictures exactly what you are doing but with 4" pipe you need 1/4" per foot pitch. You need to run the 4" into some sort of pump chamber large enough to set up a proper pump with a series of float switches to monitor the level the black water and control the pump ( in Ct...
Re: Bull's Old Barn: Gonna Need Some Help
Bull I would think about building a temp. wall inside along an exterior wall that you intend to repair. Cut the studs up a couple of feet, run pressure treated sills and then pull the walls in and sister full length studs along the old existing ones and...