Looks like the driveway isn't in good shape either. Deal with the front steps and driveway and see what you have left to spend. If you can DIY the paint it looks like you have a gray roof which means there are a lot of different colors you can use on your exterior. Multiple shades of gray, white, blue or green are possibilities. If the roof actually leans a little brown, just stick with warm versions of a color. Is there a color you have used a lot of inside that you like? Once you choose an exterior color, paint your door something more interesting than white which complements the new color. You can remove the shutters on the double window. While the houses below are different than yours, I'm just trying to give you ideas for color combinations.

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I would remove the shutters and paint the whole house a solid deep rich color to unify.

pop of color for the front door. replace with a full view glass if budget allows.

I would also build a deck across the front of the home for outdoor living.

Remove the shutters, paint the garage doors a shade of whatever color you have/use on the house, and find a nice cheery contrasting color for the front door. Done! Then work on plantings next year.

I would start with the entry area. Steps first: Face them towards the front not the driveway.

Replace front door with one with windows for a more inviting look.

Then a walk. That could run you $5 in materials.

Remove the shutters, should not be on a double window.

Have an arborist come look at the tree to make sure it is healthy. Call your state's extension service they will give you a list of arborists. Usually they evaluate for free. (Just did that here in Massachusetts).

As more money becomes available look into the the new minis splits for AC so you can remove that eyesore from the front of your home. Lots of rebates through your energy company are available.

Driveways are costly look into other options besides all that asphalt.

You might even consider removing that add-on garage. Look into a shed instead for storage.

Once all that is done it's time to choose paint colors.

Then landscaping.

It will be a great looking home once you fix things up a bit.

Enjoy!!!

I like acm’s suggestion to paint the garage doors the same color as the house. Once you’ve addressed the deteriorating steps and driveway, I’d focus on plantings to hide the AC unit. A limited color palette that complements the house color would be very striking.

Some option

How about a worldly gray for house. Can keep the white trim. Add a cedar accent panel next to door. Make door red? I’ll remove ac, it’s got central air

Replace the falling apart concrete steps and driveway. Add a railing along the steps. That will probably use up your $5K. Plan for new paint when the budget permits. In the meantime, touch up the white trim paint and shutter paint.

In my area of California, ranch houses like this were often designed and sold with shutters in place as colorful decorative accents specified by the architect. They were not an East Coast "shutters must look like they close" kind of design statement. If you want to keep the current shutters, you could add matching ones on the other front window.

Worldly Gray never had purple undertones. It is light shade of brown from yellow hue family. It would go good with cedar color.

Credit Lory Sawaya.

I like the color of your house, but don't think the red shutters go with it and a white door is boring. So, I'd paint your door a color that goes with the green siding. I'd paint the garage doors to match the siding. I'd get the driveway coated. It's not that expensive. Then, I'd add some landscaping. Then, with the remainder, you could probably add a heat pump/AC unit and save money on heating and cooling and lose the AC unit under the window.