Second guy was less doom and gloom.
I did some landscaping adjustment but some of my problem is the patio that the previous owners put in that really should have been sloped more away from the house. It's a pretty sad looking DIY patio and is on the short list to replace. But this guy gave me a thumbs up on the work I did to ramp up the ground near the foundation wall. I also put down tyvek that ramps away from the foundation wall to the side yard which is sloped away from the house.
Back to the problem, second guy recommended a water proofing barrier and to hold off on the sump pump. Currently I just had some cheap 6mil plastic that doesn't even get all the way to the foundation wall. Also, I'm not getting any seeping through the half/pony wall that separates the crawl space which you have to climb up in to, from the basement. Nor is sump pump well in the basement seeing any water. He said lets put down the water proof barrier and see where it goes. He will also ramp the barrier up the side of the foundation wall 2ft. He gave two options- 10mil plastic and a 10mil woven plastic. It's such a small space it was $780 on the low end and $980 on the high end. I took the higher end version since I use the space as storage and the higher version is white vs black so it's a bit brighter.
He said if I'm walking around in there and it feels like soup under the plastic and I really want, they can pop the barrier from the walls and put the sump in. (really, I can do that)
Looking at the break down, I'm only really paying for $150 in labor and taxes and the rest is the barrier (I'm sure it's marked up) but I figure he is buying it in bulk and I can't do much better.
He is coming at the end of the month so ping me if you have questions on how it went.