1. How do I handle this? do I need to make sure all the wood on the doors, trim, and floor have the same color stain? >>This is a matter of personal preference so there's no absolute right answer. Personally I like the doors, door trim, base and crown mold to match. They don't need to match the floor but of course they do need to be complementary. 2. If so, is it possible to stain the existing woodwork darker without an excessive amount of work ( like sanding it all the way down)? >>Yes it is despite what I've read others claim. Speak to a reputable painter who is skilled at wood finishing. Just as is used on kitchen cabinets, there are stains that can be brushed or sprayed over existing finish once it's properly prepared. As long as you're going darker, it's not necessary to sand all the way to raw wood. 3. Is wood trim and moulding considered dated, these days? >> Styles come and go. Unless you move every few years, do what you like, not what would appeal to the majority. 4. Would it be better to go with replacing it all with white composite? (Lots of the woodwork needs repair as the previous children used it as a medium for carving pictures and their names) >> If you're going to paint, damaged areas can be filled, sanded, primed and painted. Just keep in mind that the grain on the old wood might show through in the finished product. Do a test on a piece to determine whether it meets your expectation and consider the cost difference between replacement and refinishing or painting. 5. The windows are also the same color of wood, would it look strange if they didn't match the trim around them? >> There again it's personal preference. I prefer that they match. There's nothing that says you can't paint the wood.

Lucky me, I guess, because I have Kentucky bluegrass. There are endless squirrels around here. I have heard of a fundraiser for a country fire department that holds a competition for shooting squirrels. Maybe I can get them to hunt in my yard this year.

I said you need to have soil removed, because you have soil washing out over the concrete curb onto your driveway. Looking back and zooming in on your first picture I see you have a wash out situation at the front porch. So you need topsoil there but you already have a retaining wall in the front. Is that last drawing from an architect or did you make that in Google SketchUp? The drawing shows two steps down from the house sill, so that means pouring concrete up from the current porch to the top of the front door landing. They you're showing a concrete pad down to the new soil level. That means removing all the soil down 4 more inches to form the new concrete surround for the asphalt. Filling it back with concrete will bring it up to grade which looks to be several inches below the grade you have now with the washout onto the driveway. It's hard to see in the darkness of the shadow, but I don't see concrete between the red bricks and the soil. You should have at least 4 inches of concrete house pad showing under the bottom brick. Pushing soil up against the house pad to the bottom of the brick is a bad idea. The drawing shows the white add-on side entry going all the way to a new lower soil level. The drawing also shows the retaining wall being removed. So if you're going to do all that, you'll need a grader to come in and contour the soil so that it does not wash out into the street or onto the driveway and so that rain does not flow backwards into the house. And anyway, generally for new grass you don't need to add topsoil unless you have low spots to fill. I don't see any low spots. Your current soil is very likely to be fine for your new garden. If you want to tune it up you can adjust the chemistry following a good soil test (Logan Labs $25) and fix the biology with organic fertilizer. If you're trying to get this to look like the drawing, you need professional landscapers to get going before time runs out to seed grass this fall. A tractor with a box blade can break up the soil and concrete in a morning and finish regrading in the afternoon. A front end loader with a dump truck can haul the concrete and excess soil away.

The top picture looks more dense than I would expect in a Marathon fescue lawn. Is the lawn grass thick and dense when it's growing well? And are the tips of the new growth blunt instead of pointed. Does the grass send out runners over top of the ground? Here's a picture of St Augustine with the blunt tips. Or is it fine bladed with pointed tips? Runners or no runners?