Every big ticket item (long vacation, stylish automobile, new furniture, HVAC replacement in our home, etc) would have required either months of saving and planning and/or dipping heavily into savings. 

Here are my thoughts and questions on this:1) It would seem doing something in the grey or beige safe spectrum of colors would be wise, I did "Teepee Brown" on the last house, and would like try a light gray / greige color2) Grey seems like it might clash with the red brick, this brings me to 3)3) I am wondering whether or not to paint / cover the brick features shown in a white / stucco material - this will add a small amount of cost4) Note there is 3/4" Oak Floor underneath the carpet, which will reveal and fix up towards the end5) At first I considered trying to demolish the brick planter, but after more consideration it will be cheaper and easier to "roll with" the feature...

You might consider adding a small flower planter to the bottom of the windows if you can also figure out how to get a water line to them from your irrigation system.

Brilliant minds think alike, @Julia Blythe, because that's exactly what I wanted to do with those front windows - they seem to be calling out for planter boxes there.  :-)

I had mold on my wood floor when a planter leaked and was not caught for a few weeks. 

Although she loved the terraced planters, they did not want to put the time into them to keep them up. 

Choose neutral colors that will appeal to a wide range of tenants.Upgrade lighting: Replacing outdated light fixtures with modern, energy-efficient options can not only improve the aesthetic of your rental, but it can also save your tenants money on their energy bills.Update kitchen and bathroom hardware: Swapping out old faucets, handles, and drawer pulls for newer, stylish options can make a big impact in these high-use areas.

We are wanting to make something into a stylish Airbnb/personal family vacation home.

I saw a renter hanging a jacket on a swinging planter holder near the gas stove and thought, they could burn my place down.

The finished product looks stylish but clean.