This calls for a landscape expert! Many give free estimates and even pencil out design ideas - they can assess your needs in an instant - estimators can give a follow-up quote in a day. Make numerous appointments and if there seems to be a reoccurring theme and you like it - go for it! You can have them do a portion or DIY - There are so may ways to go - wood decking or pavers - especially with the ornamental grasses and succulent plantings - you desire . . .

Hard to say where or how much retaining is needed from a picture. However, a "ledgestone" style rock wall would complement the type of fence you are considering. I agree that you could use a design for this.

Hardscaping: you can terrace the deck; and/or create shallow terraces in the yard and backfill with imported soil as needed. Dirt work is heavy & time consuming if it's just you & a wheelbarrow, so once you figure out how you want this area to look you might want to contract out this phase of your project.

If you eventually decide you still want access to the street on the side the photo is taken from, avoid making the new path/sidewalk a straight line. You could buy large paving stones, or make pavers yourself out of cast-in-place concrete, to create paths wherever you want around this area of the yard.

I agree with sarahpriest that it's very bad karma to try to get free design details from a succession of landscape architects if you don't intend to hire any one of them. OTOH hiring a landscape architect start-to-finish is very expensive - a close friend has used one for years, & the most recent landscaping in his new house set him back well over $30,000. He got outstanding results but if you don't have that kind of money, Google around on the Interwebs - there are landscape design software packages that go for about $120 that might be useful to you. Once you get your hardscaping done, you can either buy garden design software, or join up for free at sites like SmartGardener, for example, that tailors the info they give you to your particular climate zone & growing season.

If you are really and truly stuck with how to begin, set aside several hundred dollars for a landscape architect to do a one-shot basic hardscaping design for you (terracing, paths, & underground sprinklers, for example), & then work off of that. It could be money well-spent.

Whatever you decide, Good luck, and Happy planting!

For ideas, concepts an plants, search here and elsewhere online for "xeriscape." There are many many options to inspire you.

You have great potential here for a beautiful xeriscaped yard. I think long, horizontal decks, then steps, in a series would look great. But I agree that you need a professional. You can hire someone to draw up the complete plan, and do the hardscape and earth moving portion for you. Then you can add the plants yourselves, saving significant money but following the plan so you know it will look right now and in the long term. You will get your investment back many times over by having professionally designed curb appeal.

What would we expect to pay for a design of a deck and/or retaining wall or a terraced deck? No idea what is within reason. Someone once quoted us $2500 just for an initial design and another $2500 if we wanted any changes - are you kidding me? What if we hated it - then we have to spend $5000 just for a picture alone and that doesnt even guarantee we like it? Thoughts?

That is pretty high for what you need. Call a couple landscape designers- not architects and get their prices. And, just from my perspective, if someone offers free designs you are free to use it however you want. We do free consultations, but have a minimum $500 charge to put anything on paper. If the client hires us we put the design fee towards the job total.

From experience…do it right the first time, even if that means doing it in stages. I read on Houzz that you should expect to invest 10% of the value of your home into landscaping. It is like putting in a new kitchen. You will get it back should you sell and if you stay for your lifetime, you will have the enjoyment of a perfect yard.

I'm very surprised to hear "Paradise Restored Landscaping & Exterior Design" encourage people to "STEAL" a professional's ideas. I agree with "sarahpriest" who says it's unethical to call someone in and have them travel to your location, spend time there and even more time preparing an estimate for you if you have no intention of giving them any work. It's no different than consulting with a Doctor or Lawyer, you are taking there ideas and opinions. Let's be more respectful of one anothers professional advice and pay for what you get.

You do not need to employ a garden designer if you spend some time working out your own ideas:

Measure out the plot and draw it on a piece of paper. Decide how large you want your terrace to be, and then put the retaining wall at the end of this. Add steps going down from the centre. Plant succulents, grasses or whatever you want to the right and left of the steps at the lower level or both levels if you want to break up the terrace with some planting. You can also plant (suitable) plants into the cracks of the retaining wall if you build a dry stone style wall. If you build a plaster wall think about using an interesting colour like terracotta orange which will go well with the kind of plants you can grow in your area. (I'm in England, we could not get away with such strong colours)

You will end up, with a level terrace by the house with an infinity view, and on the next level with manageable and more interesting planting rather than just plain lawn. Use hedging or trees at the end of the garden (as formal or informal as you like) to give yourself a boundary.

When you have worked all this out, ask a couple of local Landscape Contractors to quote for the work, and choose the one you prefer. (Best value, most pleasant, most experienced or whatever)

The more you have worked out beforehand in terms of types of hard surface, types of plants and so on the easier it will be for the contractor to price and for you to know what to look for in his/her quote.

Good Luck!

Some nurseries have designers available for this type of design work. They are much cheaper than a licensed architect. These designers use the same programs that one of the other commenter recommended. But they know more about plants than you would and therefore give you a better end result. The nursery will probably give you a discount on the materials if you use there designer and buy from them within a certain period of time.
Another option is check with any local schools that have landscape design classes. Maybe they would be willing to do the design work as a school assignment.

$2500 seems steep, but call around and see if you can get quotes for some quotes (if that makes sense). It shouldn't be something you don't like if you do a lot of looking online first, or at xeriscape books at the library/bookstore, or even drive around and take a snapshot of things you like so you can communicate the style you're looking for. Your local nurseries may have lists of native plants that will do well, so you don't waste money on plants that look nice but will die in a year. Make sure to look into your local building/landscaping codes to verify that you are legally able to do what you want too, some cities have rules regarding what plants can be used or how much can be hardscape/rocks. Good luck and don't rush it, inspiration can take a bit of time but you'll find it!

Thank you sarahpriest and gardenofdistinction for your comments regarding my advise to have myfriendsclosets call some landscape professionals. Since they did not say how much they had budgeted for this project - but did insinuate they were tearing out a road and replacing the fence (no reference to DIY)- my suggestion was to 'go the professionals'. Surely you give free estimates as a landscape expert? Your strong words are embarrassing as I certainly wasn't encouraging underhanded stealing. Obviously you have strong feelings regarding this and I apologize if I hit a nerve. We also, as Ross NW Watergarden stated, offer free consultations and a design fee that is credited to the project if hired. Also, many clients do projects in stages - I believe that was what I was getting at when i said, "you can have them do a portion" - mention of DYI was primarily for feelers (not knowing how much they were hiring to having done) But I stated it incorrectly - and have learned my lesson from your sharp rebuffs.
Paradise Restored does many estimates and we do not get every project - yes, we drive to people's landscapes, give them our time and the benefit of our expertise and in some cases leave them with some visual design ideas - hearing an idea does not a design make. It gives them a starting point and many times after an estimate - they select us for all or part or even upgrade from there . . .
It is my deep felt hope these discussions are a support platform and not a forum for reproaches. I thank you for teaching me to be more selective in my wording.

Hi myfriendsclosets - you've been given some great ideas regarding your need for help for your landscape and deck - you certainly have a lovely home and that beautiful tree is simply gorgeous! Best to you and your project!

My first suggestion is to start with an overall design plan. There is a company in San Clemente, Paradise Designs Inc,. that has been doing residential landscape design, construction and maintenance for over 20 years. They did a similar front entry lawn replacement for a client in Newport Beach utilizing concrete steps to create a more inviting entry and replaced the lawn with drought tolerant , native plantings. Most companies will give you a complimentary consultation to discuss your needs, desires, discuss budget and leave you with a proposal to do work. Check them out. Use your local talent.

Agent Orange and a sniper.