If it were me, just looking at these two pictures, I would leave the front alone for now and focus on the back. Sure, the front yard looks boring and traditional, but it looks reasonably maintained and you should be able to keep up with it without too much effort for the present.

Drainage looks like it could be a problem in back. It doesn't look like there's much of a slope away from the house. There are a number of possibilities for that, but definitely you want to look into that sooner rather than later. You might find that the best solution involves buried pipes, etc. and if so it will be easiest to do that now while the yard is bare than when you've got a bunch of stuff planted, or a patio built, etc.

I'd begin by asking you what you mean by "native". To many, that automatically seems to jump straight to some kind of meadow/prairie (same thing really) plant community, and that can be a great thing, but in what sense is it native to your area? Were there prairies where you are two hundred years ago (or whatever timeframe you choose)? Same way in my area-peeps always say they want a "native" landscape but they rarely if ever mean by that that they want a forest. Yet that was precisely the native plant community which existed here before European colonization.

I know, this just confuses things, lol, but I always like to define my terms before starting any action.

+oM

Following +om's suggestion, this seems like it might be helpful as far as choosing plants goes:

http://www.nps.gov/plants/pubs/chesapeake/pdf/chesapeakenatives.pdf

I agree with WoodsTea, especially about your backyard drainage. When it rains, does all the water run down the middle? It kind of looks like that would happen, but it could just be your photo that looks like the yard is lower right there. However, if that is the case, I'd deal with that first. Then trees, both front and back since they take so long to grow. After that, I'd concentrate on the backyard, doing just enough for you to maintain. If you make a bed, even a native bed, too large to begin with, and can't maintain it, soon you'll just have a yard full of weeds. Far easier to take smaller areas and expand them, IMO.

No to be obstinate and disagree with Woods Tea but if it was me I'd start in the front because I don't think I could live with those silly looking 'all the same size assorted shrubs' lined up like soldiers in the front planted in that tortured skinny bed. You really have to wonder when people do that. I'd start out by drastically increasing the size of that area into much wider but gracefully curved shape and take at least some (probably all) of them out to replant and create some more naturally looking layers with height and pleasant texture variations. That would make it inviting to the house rather than looking like they got washed down like tumbleweeds against the house during a flood.

I started with the traditional area close to the house and then created islands. All these got bigger every year until the lawn was so small it was easy to eliminate entirely. Its now one continuous landscape but that took place over several years. Unless you have substantial funds and access to large equipment or are able to hire help, its best to focus on areas that are manageable. As a do-it-your-selfer thats my advice because if you try to do the whole thing at once you will be over whelmed.

As areas start becoming more defined and you learn as you go about plant choices, local natives and what you want, it becomes easier to deal with and you find you didn't have nearly as much space to deal with as you originally thought. Mine now seems much too small and there are so many things I wish I could grow but don't have the room.

As for wooded or meadow/prairie, your access to sun will determine what plants you can grow in an urban area. A mix of both could work fine if there is sufficient sun in front.

Woods: We're working on the drainage issue, which we've gotten partially fixed. Looking at buried pipes, possibly draining away to a spot where we could put a water garden.

Wiscon: Probably more of a hybrid of the two, we've got quite a few trees around us, but also a fair amount of open space. Our subdivision is actually one of a rare few in the area where the builders actively tried to keep most of the trees during construction.

Edlincoln: Pretty, but still eco-friendly and good for wildlife.

We've got two big oaks, a tulip poplar, and some dogwoods; the two adjoining properties have maple and pine. We've got volunteers for all of the above!

Gardening With Native Plants of the South by Sally Wasowski is a book I have used for years. It has very useful information on actually landscaping with native plants. Some of my favorites that would be happy under your trees are Itea virginica, Clethra, Euonymous americanus, and the native hydrangeas.

I agree with the comments above about not letting yourself get overwhelmed. Texasranger's method of creating island is an excellent one.

Marti: The water ponds in the center, but tends to drain out fairly quickly after the rain stops...though the deepest parts of the yard may stay slightly damp for a day or two.

junco, I've never read that one but her book on gardening with Texas natives is a very good one. Same thing, she offers viable solutions for laying out plans in different regions.

If the back area is that wet, I'd think of ostrich ferns and cinnamon ferns.

Native meadows are very labor intensive. If you are trying to keep them in a form that doesn't look like a weedy, unmown lawn, you have to constantly weed.

What kind of maples? If they are silver or Norway, I'd pull them. If they are red, sugar, paperbark, or Japanese red, I'd keep them. What kind of oak?

Most of the time, it's actually fairly dry back there...to the point that the soil cracks in places. There are also parts of the lot that are fairly sandy. Water only ponds during heavy rains, and in summer is usually gone in a day or two.

Red maples, white oak, red oak.

Why pull the silver maples? They are native to Eastern US, and have great benefits for wildlife.
Japanese maples are not native- though I do generally like them. I like Cinnamon ferns a lot- also the Osmunda Regalis (huge fern).

I like the looks of Silver Maples myself, I think they are pretty with nice bark. The problem is the limbs break quite easily so in the city they aren't considered a good tree choice especially close to a structure or walkway, but yea, they are native. We are very windy here and maybe that factors in but whole main branches will often break off and fall during or after a storm, they are especially dangerous in ice storms.

My mom has 2 in her yard- one very large one that hangs over power lines.

Consistent to your comment- there's always debris from the large one after storms. I don't know how some of the branches have managed to not bring down the lines.

Ok, so...identify the maples and pull up any Norway maples. Save a few tulip tree. Come fall, identify and save any oaks with especially good color. Pull up any maples with bad color. Move a baby tulip tree or oak with good color to your front yard.

If it were me, I'd spend a bit of time thinking about what sort of native plant garden you'd prefer. If you really love woodland plants, you'll need shade trees and shrubs, and those should go in fairly early to provide the 'bones' of your garden. If you have more of a wildflower meadow picture in your mind then adding lots of trees and shrubs may not be your first step!

Also, think about why you want to plant natives; are you hoping to provide habitat for wildlife, or you just like the idea of natives as opposed to exotics? If you have an idea of what you want the end result to be, that should help provide a road map for getting there.

You might want to see if there's a local chapter of the VA Native Plant Society near you; I'm thinking native plant sales, and free local advice... http://vnps.org

Good luck!

Virginia

I would reshape the beds a bit and get away from the straight lines. Soften them a bit with some curves and make them a bit bigger. You may want to also plant two smallish Magnolias on the front lawn just to break it up a bit or some other native tree. A bed down the walk way would get rid of lawn lawn look. You may just want to experiment with the plants a bit. I agree with some here that you need to get rid of the plants in the front and start again. Go for color but make sure that you pick similar plant material with PH and water needs. There is nothing worse than having to pamper one plant just because you liked the way it looked in the nursery. I would also suggest maybe breaking the front lawn up with some smaller beds towards the street. You can go to the book store or online to find pictures that may give you some ideas. The lawn doesn't need to be the whole front, but it could be used to accent a rather beautiful garden.

About the back. For drainage issues try getting some Black Gypsum DG and spreading it all over the soil. It is best to till it in or just leave it on the top while you plant.This will help with the drainage naturally. Also I recommend using EZ Flow compost when planting as well as Biotone. And you can try the Humic DG as well. I don't work for these companies, I just know these products work fantastically. The back is begging to be all garden. It would be up to you what style you want and take your time planning. You don't want to go to the nurseries and buy cute things like I did and regret those choices down the line.