Since you are "next" to the bottom, I take it that there is a lower elevation, left of your lot, that acts as an escape route for water leaving your property? There seem to be basic flaws in the grading. For example, your driveway is pitched in the wrong direction relative to the overall flow of water. Without pictures, it's hard to gauge at whether the building elevations are reasonable, or make a true fix difficult or impossible. Also, details of the lot may impact the problem but not show up in your diagram. The real fix is a proper grading. One problem with your approach, so far, is that you're asking contractors -- who may not have expertise in grading and only know how to put "band-aids" on the problem -- to design a solution for you. Each contractor will likely have a slightly different solution so it will be hard to compare one proposal to the other. And since there is no promise of being paid for the design work, the effort might not be 100%. Another problem is that the band-aids may work for a time but have failure potential. (Power can fail in a storm so sump pumps may not work ... and drains clog, especially during storms. Or a monster rain can simply overwhelm the system.) The real solution is proper grading so you need someone who is capable of creating a grading plan ... a drainage engineer, landscape architect, or possibly a grading contractor. If it turns out re-grading is too expensive, you may need to opt for the "band-aid" approach.

Sorry I didn't get any notification that there were responses. You can leave a note on your ups or fedex account for where to leave the packages. Emmarene, thanks. I guess I was looking for some way to hide it a little bit from drivers coming down the road, but if it is a box or something that is always there I guess it's not that big of a deal.

@Yardvaark, yes, the grill will stay. I know it is unusual to do the cooking/dining in the front yard. If we were at any of our old houses, we wouldn't even entertain the idea of doing this in the front yard, but we are in the country on 10+ acres. The road shown on the site plan is a 12 ft wide road with 2-way traffic. The only person that lives below me is my uncle. The area between the porch & driveway is right off the kitchen/dining room, so it is convenient. What is shown on the site plan in the rear yard is a screened-in porch. We do have a patio under the porch, but is at the basement level. To grill back there, would require hauling food down the interior steps and through the unfinished basement. We did this when we lived in the suburbs and it was less than ideal even after we finished that basement. I agree having a master plan would be ideal. I tried doing a master plan and got overwhelmed. (See my response to Fori) I do have a plan in terms of "use" just not landscaping. I thought if I focused on this front area, it would inspire the rest of the design. As for the proposed uses: Back yard: we ultimately want to build a fireplace near the patio for roasting marshmallows and family time. North Side yard: This will be future (5-6 years out) parking for when the kids start driving. We are grading that area now, so we can drive to the back yard if needed. We plan to reseed with grass for now, but will have raised planting beds along the house to protect the house if someone doesn't stop in time. :) South Side yard: Not much to do here. We have 3 heat pumps that we thought about enclosing with a fench/lattice, but the only one who sees it is the propane man. We do need to build our outdoor shower at the end. Front yard: Other than wanting a flower & herb garden between the drive & porch, I don't know what to do. I'm open to ideas if you have any. To extend the thinking a little more, right now, you don't have a solid vision of what you're trying to create. It's a fact that "gardens," at times, can become a bit (or a lot!) messy. While landscaping on the other hand, tries to be always tidy. You've got that right! I don't have a solid vision! LOL! As for the garden, I was thinking more flowers with either herbs integrated into the flower beds, or a separate area with herbs. I wasn't thinking "garden" as in corn, potatoes, beans. I thought herbs were on the "neater" side of gardening and could be incorporated into landscaping easily, no? My previous neighbors had herbs growing in the foundation beds out in the suburbs and it looked lovely. Maybe they spent a lot more time than I thought tending to them?? I can't see that a fence here would be necessary or desirable. Visually, it would represent somewhat of a barrier in an area that is supposed to look welcoming. Being a MINOR barrier wouldn't necessarily be a bad thing. I want this area to be welcoming from the porch/dining room. I don't want guest automatically walking through it. I have 2 sets of doors off my porch. The first set are the teal double doors on the front of the house. The second set are the white, double doors leading to the dining room. I'm hoping the landscaping will help eliminate any confusion on which door to use. Currently, 99% of our guests go to the dining room doors. (One reason is that our temp sidewalk leads to this door.) I want to encourage guests to go to the front door. Building my main sidewalk should help, but my husband wants to keep a walkway from the side porch to the driveway, too. I hope my comments aren't misconstrued as if I'm saying a garden here won't work. In addition to functional appropriateness, gardens typically require more maintenance than landscapes. I'm bringing up these points as something to think about prior to committing to development. This is why I posted. I like to hear pros and cons that I may not think of myself. I appreciate the feedback!

Alex, a lot of my response depends on the sun exposure of the patio. For shade on anything, patio, deck, house the most important spot is to the west/southwest where the hottest sun of the summer is. The next most important is to the east/southeast where the morning sun hits--less hot but if you can keep it shady until 11 or so, that's a bonus for a house. For a house, you'd want large shade trees at some distance and closer in small trees--small being 20-35 ft. And just with the pictures you show, we don't know what's on the side of the patio where you stood to take the pictures. I'd certainly want several small trees-- for interest, beauty and the feeling of enclosure. Just to add, while shade cloth is a quick solution, nothing cools things down like leafy shade. As far as whether a border should go all the way to the driveway--it certainly could especially if you like to garden and want to see a wide range of plants/shrubs, possibly small trees as well that will give interest spring, summer and fall (fall color and berries)--and winter as well with perhaps some evergreens--broadleaf or conifers. But also keep in mind where you might want a break in that border if people often want to cut across the lawn to get to the house/yard/patio rather than walking down the driveway to the walkway. And how sunny is that strip along the fence? Many hostas won't want a lot of sun.