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).
For trim and doors, start with 1 gallon (3.8 L) of trim paint for every 600 sq feet of floor space. Purchase more at the store if/when needed. Trim is something that is difficult to calculate exactly, and it is more time-efficient to simply start with less than you need, and go buy more after you have used up the first round of paint and determined how much you will need to finish by seeing how much you have painted so far, compared to the gallons used.
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.
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.
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:
While you may choose to paint a door, ground-level window trim and other parts of your house’s exterior, it’s really a job best left to the professionals. One of the main reasons is experience. An experienced painter knows how to handle the prep work, spot problems and identify sources of future trouble, all while getting the job done more efficiently. They are also experienced with spending long hours on tall ladders. If you want high-quality work, it’s best to hire a professional painter near you. 
It’ll cost anywhere from $200 to $6,000 to hire a painter. Expect small jobs, like kitchen cabinets or trim, to run $200 to $2,000. Larger projects, like your home’s exterior, range from $1,000 to $6,000. To estimate your needs, figure paying $2 to $6 per square foot or $20 to $50 per hour. Actual costs vary considerably depending on coverage area, type of work and regional cost of living differences. 
Test different paint swatches. The last thing you want to do is paint a whole room and then decide you despise the color (yes, it happens!). Try out different paint colors on the surface before choosing the paint that you want. Buying sample sizes will help you save money. The caveat: paint color samples are not real paint, so if you try to finish or touch up a project with samples, the paint will fade.

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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