You're going to have to do an inspection of the liquidamber (left side of drive) to make sure it isn't lifting the driveway. It seems rather close to the fence and the drive. Roots are invasive and aggressive. You are coming up on Fall, so around November would be a good time to prune out the excess foliage on the olive trees. I'd also take out that cement divider between the two olive trees and plant below the trees with mondo grass for a lush look. I'd wait for December/January to trim back the bougainvillea. If you are lucky, you might get a frost and then the leaves will fall off. Frost is a good thing since the vine has about 3-4" thorns that are not forgiving, so you'll need to see what you are grabbing when you cut them. Wear leather gloves and you won't be punctured nearly as often as wearing cloth gloves. While the flowers are pretty, that plant is pretty aggressive on the skin and you will want to get rid of it if it is near anyway you sit, stand. Already commented on are all the cubit bushes...they need to be pulled out. Fence in front. You should look on-line to find out the set back from the property line for fences in the front. Your front wall might already be in that place; but you'll find out. Already commented on above is turning the entry-way into a useable garden space. You might consider it since the rose bushes are right next to the walk way and those thorns can be aggressive. In addition, the entry-way is semi-shaded and the wrong place for full sun-loving rose bushes. And...good luck. I like the house. You can turn it into something special.

How old is the roof? Do the landscaping now and then save up and change the roof in five years or so. You'll be spending that money to re-roof anyways. It definitely isn't worth ripping off a perfectly good roof just to change the colour a little.

Shutters should appear to be operable, so they would need to be as wide as the window... so if closed, they would cover the window. So no shutters on your house. I agree with taking out the boxwood that have been butchered. If you take the bed all the way to the sidewalk, you need a pocket bed on the left side. Yes to learn more about pruning the Crepe Myrtle. Ever heard of Crepe Murder? It's a thing. LOL Honestly you don't even have to prune them. We had several over 30ft tall at our last house, but you don't want one too tall right next to the house. Having lived in the South all my life, I don't have a problem with the grass since we get rain. No idea where you live, but the grass looks healthy. Unless you want to spend every weekend gardening, or hire a gardener, I would not go to the extreme of removing the grass. If there room for a wooden bench on the front porch?

I would research (by visiting) rentals in the area and seeing their condition vs rental price. Your biggest challenge will be to improve within the income possibilities of the market in your area. Cash flow will also be a consideration. So assess the area, see what upgrades would be needed to get the “income” to minimize your outflow of cash. Consider state taxes and other costs to make sure once you lease it you make some profit over outflow of cash. Older homes cost especially when routine maintenance has been done over a long period of years. Consider selling in this hot market to bank equity now for your future. Just really think things through and analyze all the pros and cons. As to drought resistant plants, ice plants near houses in this location are great and a big perimeter of them will help protect the home from forest fires. They are filled with water. Once you remove that tree, plant one that won’t get into your sewer lines or mess up your foundation. Check with local college extension office and get tips from them. Most have lists of suggested plants and trees. Aloe plants are good too. A garden and small bistro table and chairs converting driveway area to patio would be inexpensive way to boost curb appeal. I would paint exterior an off white with black trim. Black pots creating front patio and entry. If you replace roof, go with black or dark gray. You can add outdoor rug for color too. Then get driveway repaired. I put an acrylic awning over small garage door. You could do a black and white stripe fabric style awning too. I added two large modern exterior fixtures. Then aloe plants in black pots along with drought resistant plants on strip to right of driveway. A lighter exterior color would modernize your curb appeal a lot. Black trim and either a cedar front door or semi gloss black door. SW Tricorn black with SW Pure White or Alabaster for body of house. Carry that color palette inside home for continuity.