It's up to you. Outside is much harder because it requires more prep, patience, time, help, money and of course, effort. I have been painting my own houses and rental properties interiors for 20 years, and I painted the exterior of one, once. I then had it promptly done again by professionals who said it would have been cheaper if they didn't have to undo my work first. My advice is to get pros for the outside because everyone will see it.
According to Craftsman National Estimator, "High time difficulty factors for surface preparation and painting. Painting takes longer when heights exceed 8' above the floor. Productivity is lower when an application requires a roller pole or wand on a spray gun or when work is done from a ladder or scaffold. When painting above 8', apply the following factors:

The next step up is a semigloss finish, which has the level of reflectivity that makes an impression but can be challenging to apply. Semigloss paint provides great coverage and is easy to clean but is less forgiving when it comes to brushstrokes and overspray. The highest-end finish is full gloss, which looks very luxurious when the job is finished, but requires a surprising amount of prep work and painting experience to apply correctly. It is also on the expensive side, so it is often used sparingly on door frames, window treatments and accent walls.

Of course, paint brushes and rollers are also important line items on your budget sheet. A 3-inch-wide paint brush costs, on average, $10 to $20—though you'll likely need an assortment of paint brush sizes for trim, corners, and narrow surface areas. Brushes come in a variety of bristle types and qualities, and each has a different purpose. Some are intended for specific paint types, finishes, and surfaces, so be sure to buy the right brushes for your painting job.
Following the same process as the primer, cut in the walls with your chosen paint. For best results, paint one wall at a time. This makes it easier to spread the paint while it’s still wet. Work from top to bottom, rolling the paint in V or W-shaped strokes. Before applying a second coat, wait two to four hours. Then proceed with the same process used for the first coat.
Your homeowner’s association might limit you as to how unique you can be with your exterior paint choices. Check with them first to make sure you don’t have to redo your hot-pink-plus-unicorns murals. It can help to drive around your neighborhood to see what your neighbors have chosen and come up with a color scheme that fits in. If you’re not sure, stores can give you small cans of paint so you can paint patches of color in discrete parts of the exterior to see how they look before purchase.
A gallon of paint costs $15 to $40 and covers about 350 square feet with one coat. Designer varieties can run over $100 per gallon. Your contractor pays 50 percent less than what it runs in a home improvement store. You’ll also need to spend another $20 to $100 on supplies like brushes, rollers, masking paper and plastic. A professional will have these items on-hand.
Before hiring a painter, you should get a detailed estimate from them. This should include costs for labor, materials, paint, and the timeframe of the project. Covering details upfront will prevent issues from emerging later on. Ask the painter if they charge for travel time, whether their estimate includes pressure washing and caulking, and any other questions you might have.

1300 square foot house + single car garage. House on hill, 1/2 of house is 2 story, 1/2 1 story. South side of house needs LOTS OF PREP WORK! Paint peeling & flaking off. Want eves & facia white--stucco bottom white--wood siding blue grey--window trim white--and small accents, window sash, and single garage door antique white. (Sherwin Williams paint design colors). 1 base coat, 2 finish coats. Cost in CA.

Get estimates from several contractors, request and contact references, search for complaints at the Better Business Bureau[12] and check that the company is properly bonded and insured, as well as licensed in your state[13] . Only pay a small deposit, and don't pay the entire amount until the job is finished to your complete satisfaction (both painting and cleanup).
It’ll cost you between $500 and $1,000 to paint the exterior yourself. Not including paint, it’ll cost you no more than $200 to $300 at a home improvement store like Home Depot, Lowes or Menards. You may end up spending more if you buy high-quality products from specialized shops. Professionals can get the same supplies for about half what you’ll pay.
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