FIRST: Unless you can stay in business painting 1 bedroom at a time for $500-$1000, which you can't, then you will be taking on several thousand dollar contracts that require thousands in Labor and Materials to fulfill the order. Multiply that by 3-4 jobs at one time or in our case 15-20 jobs at a time, YOU NEED TO TAKE DEPOSITS!!! It is horrible business not to take deposits. There are many jobs where its not possible to get a deposit and that is built into or pricing accordingly. If we are not getting a deposit, there is a finance charge built in, contractors are not banks. If you don't have a good feeling about a deposit, your hiring the WRONG CONTRACTOR. Hire people you know or well established businesses.
When hiring a contractor it is always best to hire one who is personally referred to you by someone you trust. Hiring through ads or phone book is hit and miss. Check with your local paints stores, they know the good guys from the bottom feeders. Go to the stores that sell the high quality paints like Benjamin Moore(nonpareil), Pittsburg, Sherwin Williams or Glidden. Don't go the the big box stores for referrals, the people there don't know squat!
WOW! I think the guy I hired read this first and I have photos that would make your skin crawl. Bottom line: he got me for $1900.00. Every single thing he painted had to be completely redone....that's when I discovered he did NOT use the colors I picked, he actually used leftover exterior paint from his mother's house! Because I have pets he said things needed to be sealed first and I did agree to that. What I did NOT agree to was using some kind of foul smelling gray stuff ON MY HARDWOOD FLOORS! THEN he painted them BLACK, telling me that all they were good for was covering over with laminate or carpet. He also dripped and tracked paint all over my ceramic tile floors. PLUS left a wet used paint roller in my garden window and had stuff piled in front so I didn't find it until it had dried. I have no idea how much that is going to cost to repair. Then he left without finishing (thank God) but left the "leftover" paint, uncovered, in the rain. Again, hid it so I didn't immediately find it. Obviously we will be going to court but I doubt if I see a penny from him.
Depending on just how dirty the outside of your house is and on the house's size, there are two ways to approach this job. If you live in an average-size house, use a garden hose with a carwash brush attachment to bathe the big areas. For caked-on dirt, use a scrub brush or a sponge and a pail of warm water with a good, strong household detergent in it. Work from the top down, and rinse all areas where you scrubbed with water.