Tips needed for exterior house painting

I have a 1.5 story home, http://www.dongardner.com/plan_details.aspx?pid 3
that has original paint from 2000. I'm pretty sure it's ready for another as the caulking is cracking and the coverage looks thin.
I live in a somewhat humid area -- NE KS.
What would be the best time of the year to paint? What weather conditions?
What would be the best paint? I hope this lasts another 10 minimum.
Should I hire a pro? How do I select?
Should I do it myself --- seems like a 4" brush is my most likely choice.
Do I recaulk over the old caulk/paint? Or dig it all out and start new?
What sort of prep should I do?
Feel free to direct me to links, etc
Thanks in advance,
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wrote:

I've always found that clear days with moderate humidity and 50F to 70F works best, when it doesn't get down below freezing for 24 hours, or so. The idea is to pick a day when the paint dries completely but not too fast. You want to maintain a "wet line".

I like Benjamin Moore, but Sherwin Williams has a good rep, too. Spend real money on paint. It'll pay in the long run.

Your choice. I do it myself. I can't see spending thousand$ on a pro. I'd rather spend that money on toys. ;-)

My choice. That and a 2" or 2-1/2" brush for trim and edging. I prefer angled bristles rather than straight cut.

Anything that's loose has to come out. There is no reason to pry out good caulk, though.

Depends on the condition of the surface. Roughing up the old paint with a wire brush (will help find loose paint, too) and a good bath is a minimum.

I've always had good luck with answers from the people staffing a *real* paint store.
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The only thing I would add is , taking on a WHOLE house as your FIRST real exterior paint project could be a costly mistake and leave you very discouraged..If you also work a regular job you will be lucky to finish it this summer....Oh , one more thing...You're gonna need ALOT more than a 4 inch brush and caulking gun..That is unless the whole house is less than 6 feet tall....
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On my Vermont house I painted one side a summer. I also sided one side a summer, but that's a different story.

Ladders are cheap, too. ...even good ones. Buy nothing else.
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As SLOW as he will be going renting will cost as much as buying...He WILL need more than one ladder and probably pump jacks...Even I wouldn't attempt to paint an entire house alone part time...I would atleast hire a couple helpers...Putting up pump jacks alone is scarey at the very least...Trying to do it ALL off ladders is PAINFULL on the back and feet as well as slow and depending on the paint used , it will look like shit with that many over laps...
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Did you look at the house? Practically all the painting except for the dormers is 1 story. No way does he need pump jacks. One extension ladder to get the dormers and one or two folding ladders will be fine. Looks like more time will be spent on trim that siding with all that porch space.
It is a lot of work for one person but if you really devote plenty of time to it you can be done in a few weekends. I'd start as soon as the weather permits to avoid the heat of summer. Not to keep the paint out of the heat but to keep you out of the heat.
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Most important tip is the same as for any paint job: prep work. You need to scrape away any peeling paint and prime any of those areas. And you need to make sure the surface is clean and free of all dirt. For exterior, that usually means power washing it. That brings up it's own set of issues, #1 of which is to be careful, not use too much pressure, or you can damage the wood.
Best weather is moderate temp days, eg Spring and early Fall.
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No need for pump jacks. Extension ladders work for all but the most difficult houses and there pump jacks won't help anyhow. It doesn't take *THAT* long to paint a house.
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