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.

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While vinyl siding salespeople claim it never needs to be painted, it does lose its color strength over time, and the degree of fading can vary depending on which sides get the most exposure to sunlight. Perhaps it still hasn’t faded, but you don’t like the color much. You can’t go any darker than its current color, though, because the siding is designed to absorb only so much heat, and a darker color could cause it to buckle. Vinyl paint is available in many colors. Brush painting and roll painting vinyl siding costs $43 per 100 sq. ft., and spray painting costs $34 per 100 sq. ft.
Premium Plus Interior Ceiling Paint 1 gal. features Premium Plus Interior Ceiling Paint 1 gal. features a durable, acrylic-latex formula that is specifically designed for use on previously painted or primed interior ceilings. This spatter resistant formula minimizes glare and provides a mildew-resistant finish. This formula also maintains the original acoustical ceiling properties.  More + Product Details Close

The average cost to paint the interior of a house or room is $1 to $3 per square foot. Painters charge $1,200 to $3,900 to paint the walls in a house interior, and the cost to paint a room is $350 to $850. Prices increase when including the ceilings, baseboards, and trim. Get free estimates from interior painters near you or view our cost guide below.
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.
Interview past clients. Talking to former customers is always a good idea. But, to ensure you're getting honest feedback — not just feedback from people who have been handpicked by the painter to sing their praises — ask to speak to the painter's three most recent clients. When you speak to them, ask about specifics. Find out whether the painters showed up on time, protected furniture from paint spills, kept the house clean, completed the project on schedule, and of course, what it cost to paint their house.
At least 90% of painting time goes into setup, prep work, and priming. The method of prepping required varies for each type of exterior material on the home, but every project must be patched and cleaned. The more thoroughly you prep and prime your home’s exterior, the longer your paint job will last. You could save quite a bit if you do this part yourself, but it must be done correctly, or your contractor will have to go over what you missed. The prices mentioned are based on paying a contractor to do each job rather than one overall quote for the work from start to finish.
Prepping a house costs anywhere from $0.50 to $2.50 per square foot. This is almost always included in the total project price. However, the DIYer might negotiate some discounts for completing this work on their own. Be warned, proper prep is key to the quality and durability of the finish. If you do this work yourself, the contractor might no guarantee to finished product.
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