Any advice?

Need to do this by the end of the summer.

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Lay off that whiskey and let that cocaine be.

Go to a roofing supply company and dumpster rental firm to find out the actual costs of the supplies you'll need, then hope you can find friends with referrals.

The last time I did my roof, a friend's sister knew some Polish guys who did excellent work and even changed a downspout that has proven to be excellent for the last 10 years.

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There are only two examples of infinity: The universe and human stupidity and I'm not sure about the universe.

Dumpsters are expensive as shit!!! I got one for my roof and at least they had a discount for asphalt shingles. It was still a good 450 IIRC. A dumpster of the same size for just debris was like 750-800. I think with materials i paid 4k for everything. I have a compresser and a roofing gun so I spent a week kicking its ass and saving myself 6-8k. I have no desire to do it again. Roofing is not fun....roofing by yourself is all that is hell. I want to say i did it during a 4 game series where the Cubs played the Giants in 2015 and the Cubs swept and it propelled them into the pennant race...so at least i had that.

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That's my purse! I don't know you!

If you're doing a full tearoff, you might call your insurance company to see if they offer a break on premium for a new roof.

I guess PSA to anyone ... if your roof is ~7 years old or less, take a moment to find out if you can catch a break on premium. Possibly as many as 10-12 years too but the savings, I would presume, would be minimal if they existed at all.

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Power is always in the hands of the masses of men. What oppresses the masses is their own ignorance, their own short-sighted selfishness.
- Henry George