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Sadly if you plan to keep the place, do not cut corners here. Yes to do it correctly is VERY expensive but, done wrong can often be FAR more expensive by the time you find out something was done poorly. If you are planing on keeping the house for a while finance having it done right the first time.
 
I've done two roofs and multiple shingle replacements, etc.
Yeah, its a lot of work. Degree of difficulty largely depends on your pitch.
You can do it in sections, the bad sides first.
If you can separate your shingles, you can repair the add-on joint. However, if you have dry rot, a fungus, you need to get it removed or it will continue to spread.
My first roof had bad rot that was not visible. I post-holed it and put my leg through the master bedroom ceiling.
On the second job, I had two highly recommended roofers out and dismissed both from consideration after encountering them or seeing their work examples on other houses. If you get quotes, ask for examples of their work. Many roofers have no clue how to do complex valleys or junctions.
Good luck to you and your wife with her hip. Sounds like the both of you have been through a lot.
 
Have an experienced crew tackle the job after saving up and ensure you get concealed fastener metal roofing (custom fit on the job), ice and water shield, and 15# felt over the shield. Depending on the roof pitch(es) make sure the seams are properly sealed as necessary as per manufacturer recs. Absolutely check the bid and see what kind of fasteners will be used and make sure they are of proper length, diameter, treatment, etc. If caulking is used as a primary means of leak prevention, your new roof was a waste of money.

And finally, don't fall for the roofer who claims his work is best due to being "hand nailed"... they're too cheap to buy quality pneumatic tools or don't trust their laborers to operate such equipment properly.
 
The reason I ask is because I have some perfectionist tendencies. While I've never roofed a house, I have done smaller projects before, and they've always turned out well. I don't do halfway, and I don't cut corners. If I decide to do it myself, it will be done right, or I won't do it.

I suppose I could have just not asked at all, but a guy's got to start somewhere...
Some things are better left to 'experts'. Ever hang sheetrock in a house? What the companies do is to finish in a week. You do it and it takes 3 weeks. Do not hire the least expensive bid. Look at the ones in the mid-range bid. Roofing is difficult work. If you have leaks you'll probably have to remove all of the current shingles to find the damage, replace the damaged plywood and flashing before you can lay down new felt/paper and the new shingles. $10k is not unreasonable anymore for a new roof. Do not choose the least expensive shingles either. They won't last in the wind, and then rain can get underneath. Good luck

How many layers do you currently have on there now? Code in OR is usually 2, after that all must be torn off.
 
We just had new composite roofs put on the house and barn. There were two composite layers so that was more work for the crew to get off... In addition, some visible weakness or forthcoming rot in places in the fascia boards and plywood. We also had them remove some skylights, and put new skylights on the two we wanted to keep. ...and then new gutters for both the house and barn.

It all added up.

We had things looked at in late March, bids in April, but the work didn't start until July due to the unusually-wet May and June.
 
Not an average do-it-yourself project. I learned at the elbow of master craftsman. Top quality material is important. Recommend new waterproof underlayment rather than 30lb rolled felt. In Oregon there are shingles pretreated to combat moss. Big expense is disposal. Some companies charge extra for non-bio-degradable debris. There are reputable roofing companies and guys with tools. Architectural shingles hold better than three tab. Metal roofing costs more but is a lifetime product. Sometimes you can save a little if you buy the material. Purchase should include putting shingles on prepped roof. Don't recommend putting new roof over old. Tear off a pain, but reveals potential damage. If you are flexible and patient it can be done by homeowner. Read. Watch Youtube. Then hire it done.
 
Look at it like this. There's businesses that are in business to do work in the area that they have the business. I have done carpenter work, general contractor work, roofing (hot tar, shingle & rubberized), plumbing and sewer work, electrical and painting. It's not about whether you can or cannot do the work. It's about having enough knowledge to know when to let someone else do it. I always suggest tearing down/ removing the old. Checking the wood underneath. Making sure there is not damage to the roof and supporting joists. Also plan for the worst. So as example: you think just shingles and done? Nope expect joist and wood. They say (contractor) $8k… think $12k… a roof (depending on material) is @20-25 years IF properly maintained!

Good luck and I hope it is smooth for you!
:)
 
Thanks everyone for all the input and advice. I'm going to do some more learning and get some estimates. I have a life-long friend who builds houses for a living, but he's four hours away. He said if he were closer he'd take a look and walk me through it.

If you are planing on keeping the house for a while finance having it done right the first time.
Good question. We may end up leaving the state for greener pastures soon, but that's a big step for us as my wife and I are both life-long North-westerners. We could buy a pretty decent place outright in many other parts of the country, with the equity we have in this house. I'm not going to take on more debt. I'll take it out of savings, or sell my gun collection if I have to.

Good luck to you and your wife with her hip. Sounds like the both of you have been through a lot.
Thanks, I appreciate that. It's just life, and sometimes you just have to roll with it and keep going. I learned a long time ago that everyone goes through tough times to one degree or another, at some point in life. It doesn't take much looking to find someone going through a lot worse. Self pity doesn't do anyone any good.
 
Good question. We may end up leaving the state for greener pastures soon, but that's a big step for us as my wife and I are both life-long North-westerners. We could buy a pretty decent place outright in many other parts of the country, with the equity we have in this house. I'm not going to take on more debt. I'll take it out of savings, or sell my gun collection if I have to.
However you have to do it just do not half way it if you plan to keep the place. Let water get in under things for long and you are no longer looking at just a simple new roof. Water gets into walls and such and soon you have disaster to repair. Sucks but its just one of those things that you do not want to be kicking yourself 5 or 10 years from now when the "fix" is 10 times what it costs now to just do it right.
 
We had a shingle and tar paper roof that lasted about 16 years. It wasn't leaking yet but had it replaced with plywood and composite shingles back in 2014 since cedar shingles are very pricey.

All of homes by the home builder were shingles and tar paper so everyone in our neighborhood replaced with plywood and composite shingles which is very pricey. I spent almost $24k on my roof for my home back in 2014 but my home is a bit over 3000 square feet.
 

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