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I feel that its time for my house to get new gutters. The current ones leak, don't drain completely, need very frequent cleaning, and the damn tree rats chewed through the leaf guards in many places.

I have gotten two estimates (from the same company) so far. These estimates include new seamless gutters, leaf guards, and wrapping my trim in vinyl. The first estimate included removing dental work and replacing it with composite then wrapping the other trim and reattaching the new composite dental work. The second estimate was just to wrap everything including the dental work. Both estimates are quite high, $7500 and $6000 respectively. This also includes wrapping the trim around my small (15x15) front porch. I think I can save a LOT of money by just painting and patching the wood trim instead of wrapping. That also lets me keep the small styling details I enjoy.

My question is what do I do about the wood trim? It needs painted in several areas and possibly replaced/repaired in a few spots. How do I determine if its more cost effective to maintain the wood or have it wrapped in vinyl?

Is the following list the correct order to take to complete this project?

  1. Remove old gutters myself
  2. Paint myself (or hire a contractor)
  3. Have new seamless gutters, downspouts, and leaf guards installed

What timing issues do I need to worry about? With 3 major tasks involved, the completion of one is dependent on the other.

Do I need to worry about weather? Obviously a rain with wet paint is bad. If my house goes without gutters for a week waiting on a contractor, will that be a significant problem?

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It seems like you already have everything figured out, what is the question? Are you just trying to figure out how long you should give yourself to paint/repair the fascia? –  Tester101 Oct 19 '12 at 15:48
    
I'll make an edit. The questions are: Is my order of operations correct? What kind of time constraints should I plan for? How badly could weather derail this project? –  Freiheit Oct 19 '12 at 15:57
    
Is this question too broad for DIY? Maybe I need to break it down to several separate questions for each phase of the project. –  Freiheit Oct 19 '12 at 16:10
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1.) Yes. 2.) More detail is required (linear footage of fascia, amount of time each day you can devote to the project, average painting speed per linear foot, how much fascia needs to be replaced, how long does it take to replace fascia per section, etc.). 3.) See Murphy's law. –  Tester101 Oct 19 '12 at 16:22
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You shouldn't just try to calculate this based on how long it will take you to paint the fascia one time. Consider the fact that you will need to paint it and repair parts of it every couple of years forever if you don't get it wrapped. My advice is to spend the money to get it wrapped.

To answer your questions more specifically: Pull the gutters down and paint when the forecast looks nice. If you get some rain, or even a storm, before the new gutters go up, that's no big deal. It's constant runoff from your roof that would eventually cause problems.

Don't forget that your old aluminum gutters may have some value at the local scrapyard.

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I'm assuming by wrapped he means to rent a break and bend some aluminum around it. That's my recommendation too unless you want to be re-painting them every few years. –  RLZaleski Apr 4 '13 at 14:09
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