I don’t know if anyone in Greenwich still paints his own house but here’s a decent article on how to do it. I learned how to paint when I worked for Charley Ford back in high school and college and probably painted at least fifty houses with him and under his tutelage. Here are a few things I learned:
Preparation of the surface is 85% of the job. When Pal Nancy and I moved to Maine into an 1835 farm house, she seemed a bit impatient when I spent 3 weeks apparently doing nothing but in fact I was sanding, filling nail holes, replacing rotten bits of trim, etc. etc. and, finally, priming. I promised her that the final coat was going to take just a few days and by gosh, it did. That was an extreme example – the house hadn’t been painted in decades, I suspect, but still, it’s all about prep work, if you want the job to last.
Use quality equipment. A cheap paint brush is an abomination. It won’t hold paint like a good one will, so you’ll be slowed down, it will drop bristles into your paint job and in general, drive you friggin’ crazy. Buy the very best brushes you can find and you won’t go wrong. Natural bristles for oil, nylon for latex, but pay the money for the best. And, while you’re at it, buy a brush cleaning spinner so that at the end of the day when you clean your brushes (and you must) you can spin them dry and either return them to their cute little covers or wrap them tightly in newspaper to hold their shape. Proper clean up at the end of the day will reward you hugely the following morning. Don’t just dump your brushes in a can of turpentine or water overnight – treat them well and they will return the favor.
Use quality paint – or stain. I always had good luck with Benjamin Moore paints and Cabot stains, but these days I see that Consumer Reports top rates Baher (sp) products, sold at Home Depot. Use what you like, but for heaven’s sake, if you’re going to go through all the effort of painting your house, don’t cheap out at the end and buy some discount crap that’s going to fail in just a few years.
Do all this and you’ll have a nice job that will save you a ton of money. But now, a confession: I was up on a ladder painting Pal Nancy’s and my house maybe fifteen years ago, and looked down at the hard asphalt driveway thirty feet below and started figuring, “hmm, I make my living using my brain and if I fell and hit my head …” As a teenaged painter, I was always falling off ladders, reaching just one step too far off the rail, trying to cover a spot before I had to climb down and move the ladder, but you bounce pretty well at 17, not so well later. I finished that job but I haven’t done a house job since. Still, if you’re young and ambitious or, better yet, have teenagers, you can get decent results following these simple tips and those in the NYT article I linked to above.