I'll never forget driving into a large estate yard twenty years ago and witnessing a home owner sitting in the middle of the lawn crying her eyes out. She had always wanted a big beautiful yard but it had become so overwhelming she was completely beaten by it.
I believe a lot can be gained by paying attention to some of the best Gardners in the world - The Japanese and the English.
In Japan the goal is to only take on that which they can make beautiful; bigger is not better. It's what they can maintain.
For the English you see the philosophy that wild is okay - but layer the yard so there are areas that are very well maintained and then a boundary depicting the next area that is allowed to be wild.
When designing and re-designing your landscape; keep these philosophies to the for-front of everything you do. How much REAL time do you have for maintaining the yard? How can the yard be designed in layers to allow you to enjoy the yard but not be beaten by it.
If it's a wedding then we start at the front, skip the sides and move to the back where everyone is going to be seated. Put the most effort into that area that is seen the most.
The next rule is to create an area YOU look at the most and take extra time to make it beautiful. A couple of things to avoid:
The water fall into a pond; is it really going to be seen, heard and appreciated? If so make it a pond less water fall so trash and leaves are not a constant maintenance headache.
Too big a lawn - create a border and section the property.
Too many curbs and sidewalks to edge - put in rock next to a driveway or create a flower bed that can be sprayed with weed killer once a month so you don't live on a line trimmer every Saturday.
Too many roses and tough shrubs - how often do you really want to prune?
Landscape needs to be done in a way that makes your life as simple as possible - I so often hear someone say they are selling the home because the yard is just too big. Done right a yard is a wonderful thing to enjoy. That is the test; do you enjoy your yard?