Can you extend the patio to go the length of the house and out far enough for a large BBQ/bar space. Then you can add lounge seating along the length. Then "tier" your yard. At the base, where the water run off will go, you could do a bed of river rock. It sounds like you have a lot of shade. You could do hosta beds, astilbe, columbine, hydrangea, and other shade loving plants. Get the hardscape and tiers built. Then get the rock. Then go to your local nursery and buy (do some research for your zone and style). Be sure to use landscaping fabric for weed control. Then mulch to retain moisture.

Here are some pics. clockwise: the only flat area of the yard; the view of the shed - see the huge puddle between the patio and shed?; the view of the back from the flat area - see all that ivy?; the view of the yard from the patio

And a couple more pics - the view of the patio from the yard, and view of the yard from the middle of the back fence.

Definitely try to get some areas sectioned off with hardscape structure to deal with your drainage issue. Can you trim up the scrubby trees? They are blocking the light hence the lack of grass.

I think you could increase your patio. Take out the scrubby trees and replace with a bed of shade loving plants.

Can you build up and use a tiling system to get rid of the wet spot? Divert this water to my suggested rock bed.

We definitely know we'll need some grading done and a better solution to the downspouts. I'll look into bubble boxes for sure. I noticed when I took the pictures tonight we get huge puddles behind the raised shed, so that area needs to be addressed as well. *sigh* It quite possibly could be a much more expensive project - more like $10K. That's depressing.

Actually Jane, if you get a good landscaper out to your home he should be able to come up with a drainage plan that is reasonable. You might even consider installing a rain garden to help control the water runoff. Here is a link to get started: http://www.thisoldhouse.com/toh/photos/0,,20180459,00.html
Here is a search on houzz: http://www.houzz.com/photos/landscape/rain-garden-

Edit: Here is a sketch of a basic rain garden

Here are a bunch of rain gardens (easy to do, not expensive) :)
https://www.google.com/search?hl=en&q=residential%20rain%20garden&qscrl=1&revid=1018662419&tbm=isch&emsg=NCSR&noj=1&ei=7m91U9GpEIybyASO4YDYCg

For what it is worth, we did exactly what catlady999 suggested done to our downspouts a year or two ago. We did hire the work out and it was really reasonable. We have a slopped backyard and we had all the water piped to just before the back fence. It helped drainage quite a bit. (And, I think it looks much better then the concrete at the bottom of most downspouts).

The black tube is called tiling. And you can DIY, but remember to call before you dig. Also you can pay a pro to make this plan and landscaping and you can still DIY the rest.

Okay, so what about this? There are three trouble areas with rain run off - I've got them all leading to a pond area in the back of the yard at the bottom of the slope. Extend the deck and put in steps leading down to pond area with seating. Clear out all the ivy and try our best to extend the grass area down into that corner. Cut out the smaller trees but keep all the big ones for shade. Add pavers on the side of the house where the gates are as well as leading to the shed.

This would be a multi-year project unless we get on some HGTV landscape show. *lol* I'm thinking start out with tree cutback and the rain gardens to help with water runoff. Then the ivy. Then the pond. Then the extended deck. Thoughts?

Jane, it is a good idea to get a landscape professional in to at least assess the issue and come up with a plan that you can implement over time by yourself through DIY methods. From here we don't know critical details of your yard that may make a difference in your plan.

I did find an idea book for you that has several ideas for handling soggy soil in addition to the rain garden idea. Don't get me wrong, I like your plan but I don't have any idea if it will work or not because of the specifics of your yard that are unknown. Those conditions can only be determined by someone that is actually there to see it IMO :)
https://www.houzz.com/magazine/10-solutions-for-soggy-soil-stsetivw-vs~19793405

Found another Ideabook on planning rain gardens
https://www.houzz.com/magazine/protect-a-precious-resource-with-a-rain-garden-stsetivw-vs~3417403

Hey there, folks! Thought I would write with an update on what we've decided to do with our backyard.

1) Tree company came out and determined that we had 4 trees that were either dead or in the process of dying. We're having those removed this week. He is also removing the 5-6 "upshoot" trees that have only started growing in the past two years or so. He's removing two sweetgum trees at my request (I hate those stickerball things they dropi). The rest of the trees he will trim up and clean out for us. The result: we'll be left with the six biggest trees, with plenty of shade but without having them hang so low into our yard.

2) We are definitely expanding our patio, and have confirmed a measurement of 22 wide across the back of the house and about 14 feet deep. We may even go 16 feet deep because we can still keep the trees at 16 feet deep!

3) We are in the process of ripping out the ivy bed. We're about 1/3 of the way done with that. We discovered poison ivy along the left fenceline, so we're dealing with that before we go any further with that project.

4) I will have two rain gardens drawing water away from the house. Each rain garden will draw water to one of the big trees which I will encircle with a very basic bed of mulch.

5) At the bottom of the hill along the back fence and curving around where the ivy used to bed, I will be planting a total of 10 mountain laurel trees which will eventually become a privacy hedge. I spoke to my back neighbor about that plan to get her feedback. She said she loves mountain laurel and will not mind if it grows over the fenceline- she said if it gets oppressive she'll just bring out the hedgeclippers and keep her side short. I'm not worried about the left neighbors since they already have a hedge on their side of the fence.

6) Once the mountain laurel is in I will install a large rain garden leading from the front of the shed (the upper part of the hill) leading down the slope toward the first couple of mountain laurel trees.

7) We're still debating what to do with the backhalf of the yard where nothing grows - husband is contemplating having steps from the new patio that lead down to a SECOND patio with a built-in firepit. I think that's a marvelous idea, but we'll wait and see. I don't want to get rid of ALL the potential green space.

I've attached two new graphics - one that more closely shows what we have going on right now. And one with the new plan (and possible future patio/firepit).

Another update!

1) Tree company arrived yesterday and cleared out the trees while I was at work. It is so open now – it’s amazing. The only bad thing is the tree removal exposed a few things – there are many more “treelings” that were hidden in the overgrowth, and the tree service did not remove those. They are smaller trees – trunks are only 1-2” thick, but still something that I now have to remove. In addition to that, the removals exposed even more poison ivy, this time on the other side of the yard near the shed. *sigh* Amazingly, the backy section of the yard where nothing ever grew now gets afternoon sun, so I’m hopeful that we WILL be able to grow grass there now. We’ll give it a shot in the fall and see what happens.

I forgot to take pictures last night to show the before and after with the trees gone. I'll try to do that tonight.

2) I’ll be removing more of the ivy this weekend, weather permitting. I’m trying to locate a local farmer who will let me rent a few goats for a couple days to help clear it out, but I’m having no luck. So looks like it's just me and some roundup.

3) Now that the trees are gone my husband is concerned about the lack of privacy along the back fence – I told him the mountain laurel I’ll be planting will alleviate that problem entirely. Since their house is at the bottom of the hill, having even just a 5 foot tall hedge will pretty much block them from seeing our backyard even when they are looking out their second floor windows.

Another update with pictures! Finally had a chance to load up pictures post-June tree removal. This Friday a landscaping team is coming over and will be creating the clean slate that we need to go forward with landscaping. But these pictures show the difference even just removing some of those heavy, overgrown trees created! I'll post more pictures of the true "clean slate" over the weekend once the landscaping crew has done their thing.

Okay, the landscaper finally came today to clear out the rest of the yard. The yard looks HUGE now! Hopefully the top two left and right show before and after of the fenceline all cleaned up. The other two pictures show the clear path to the shed and the fact that the ivy is GONE GONE GONE! As you can see, even by removing many trees from our backyard we still have plenty of shade from the remaining trees as well as the trees of our neighbors.

Almost done! Landscapers have worked hard over the past several weeks. Here are pics of one section - near the shed. We laid down a LOT of mulch since nothing can grow due to heavy tree canopy. Re-laid the original flagstones from gate to patio, and then new flagstones from new section of patio to the shed. Relocated two blueberry bushes and one butterfly bush into the open area to the right of the shed (they are hard to see - but there are definitely there). New grass seed was laid down on Friday, so in a few weeks I hope I can post new pictures showing the entire space - lush and green and clean. The photos below focus mainly on the area between the house and the shed. The gutter extender will eventually become a rain garden leading to our apple tree (just outside camera frame) once I gather the materials for it. Also pictured is our new patio set complete with firepit table. Woot!

Jane S - How did your plan work? Did you start on the rain gardens in 2015?

We did not do the rain gardens - it turns out the constant wet spot just behind our addition was actually a tiny hole in our irrigation line - the guys that came to add more sprinkler heads fixed it, and the need for a rain garden in one spot disappeared.

In the other spot, the rain is finding it's way down to our back fence, which is heavily mulched and now lined with hedge plants that we planted in the spring. We are hoping they grow quickly over the next 2-3 years to create a privacy hedge as well as drink up all the water that now flows and fills in that area. We have not had any issues with rainwater flowing into our neighbor's yard, which we were a bit worried might happen.

We still have an issue with the grass in the yard not growing - despite our best efforts, any lawn we create is quickly taken over by wild strawberry. It is truly the most pernicious pest plant I know.

Interesting! Glad you found the hole in the irrigation system before you built the rain garden. Good luck!