My fear is I'd step back and see my weekend work is patchier than my attempt at a beard and they'd ask for their money back. haha
Painting is dead ass simple so long as you understand some basic things and throw out all the crap they have at Home Depot. For rolling, only buy lambs wool covers, for exteriors you want 9" for stucco and wood siding with a thickness of about 1.5" to 2". For gutters and other small trim areas, windows, gutters and such, use a 4" roller out of a two gallon bucket with 6" screen. For the nine inch roller use a 5 gallon bucket with a nine inch roller screen. Don't ever use those stupid ass rolling trays, they hold no material, expose the material too much which causes it gas off pretty quickly and get tougher to roll as it dries out. The five gallon bucket I would fill to just above the bottom of the rolling screen. Never submerge the rolling head, just dip and roll off, dip and roll off, do this two or three times quickly and you have a mostly drip free head with as much paint as it can hold. Three or four quick dips and wet rolls on the mid wall and I have enough material to roll out one area four feet wide by the normal nine foot ceiling. You can get pretty quick and clean at this after rolling out a couple walls.
That is just one of the major things that cost less than $100.00 (two five gallon buckets, one two gallon bucket, screens for both buckets, 9" rolling frame and a 4" rolling frame and a couple different thickness lambs wool covers, two or three 4' x 16' drop cloth). Kick it up a level and another $100.00, buy two window masking machines from 3M, have one setup with 9" paper the other with some 3M window mask, I usually use the 48" to cover windows, ceiling fans and lights, and two cases of beer for when the job is done.
Painting is honestly easy, it just takes a bit of understanding, knowing when to add a bit of water to the paint when it is getting thick and not rolling cleanly. Most of the streaking you see when the paint is wet will go away when it dries unless you are making a fairly big color change, then just use a proper sealer first and two coat that bitch.
For $1,500.00 more you add in a Graco paint rig and get that paint on there so quick it make your head spin. For exteriors, I always spray the paint on with the rig and have some one come behind with a nice 2" thick cover, lambs wool of course, and get that paint nice and even. Now the job is done in a day and the paint is applied cleanly and evenly and with less material used; unless your helper for the day that is filling the spray rig is a total moron, moves the spray line so that it rests on the exhaust of the motor and ten minutes later blows through the line and displays for the neighborhood what 3,000 PSI of paint looks like coming out of a 1/2" line.