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.

From dull to shiny finishes, paint comes in several different lusters. A paint’s luster depends on its mixture of pigment, resin, and additional ingredients. If you’re struggling to decide what finish you want, note that glossier finishes tend to be more durable and washable. Flat paint, on the other hand, is better at hiding surface imperfections. Pearl and eggshell lusters fall somewhere in the middle, as they are more washable than flat paint and partially hide irregularities.
Repainting is key to maintaining exterior house paint. The material that your home is made of affects how often you should repaint. For instance, wood-paneled homes need to be repainted twice as often as those made of stucco. Environmental factors also play a role in how often you should repaint, since harsh climates can be hard on a home. As a general rule of thumb, homeowners should repaint their home every six to ten years.
Plan the workforce. If you intend to not hire a professional crew, you'll need lots of help. There are many jobs to be done. First there's the furniture moving, then wall preparation, floor covering, materials gathering and prep, cleaning, and don't forget everyone will have to eat. It can easily take a team of five people a full ten days to paint a two-story (approx 2000 sq.ft.) home. Get as many people to help as you can. If some can only come one or two days, great. Maybe others can fill in. Ensure you plan with your workforce members in mind. They'll need plenty of time to arrange days away from work. Identify a few key personnel:

Needless to say, an exterior paint job tends to be more complicated. Indoors, you don’t have to deal with the elements. When painting the exterior of a home, however, you have to think about tough to reach places and the unpredictability of the weather. If you just want to repaint your front door, we trust that you’ll be able to do it yourself. Contrarily, a full exterior makeover requires professional help.
Paper drop cloths: $3 to $5 for 9x12-feet. Paper drop cloths provide a cheap way to cover furniture or windows while painting small, indoor jobs, such as touching up window trim. They're absorbent and textured to hold paint. When you're finished, you can just fold them up and throw them away. However, paper cloths are not the best option for protecting floors since they can tear easily.
Each type of siding will need to be treated differently when it comes to primer and paint at different price points. Exterior paint costs between $35–$80 per gallon depending on the quality you choose. It’s not always true that the more you pay for your paint, the longer-lasting your paint job will be, but you do need to be careful when researching exterior paints to make sure it can weather the local elements well.
However, some water-based paints are easier to work with than others. The first coat of paint may not provide complete wall coverage, or the color may not be quite as saturated. Some of these problems can be addressed with a separate primer coat, but this is a time-consuming project. The ideal solution is using a higher-quality paint that combines a primer and a finish paint in a “one coat” product.
Paper drop cloths: $3 to $5 for 9x12-feet. Paper drop cloths provide a cheap way to cover furniture or windows while painting small, indoor jobs, such as touching up window trim. They're absorbent and textured to hold paint. When you're finished, you can just fold them up and throw them away. However, paper cloths are not the best option for protecting floors since they can tear easily.
Begin prepping your walls by removing any outlet covers or lighting fixtures (if possible). Next, inspect your walls for any defects. If you encounter cracks, dents, or holes in your walls, simply fill them in with caulk or spackling compound. There are also a number of DIY tips to fill nail holes. Once your repairs dry, smooth them down with sandpaper and wipe the walls down with a damp sponge.
When determining the total cost of a home’s exterior project, you’ll want to include things like the trim, a garage, foundation, windows and doors. All work is calculated by square footage and sometimes by the linear foot, such as in the case of trim. Your contractor will give you a price for the entire project unless you specifically ask for each item separately.
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