Huge home repair - do before selling or not??

It sounds like your home can be listed is a “fixer” so I would not fix the roof. I don’t think you would get back what you put into the new roof, based on the other items that also need to be done.

Good luck and hugs! It is a huge task.

I doubt that any home inspector is going to pass that roof and gutters, so you are probably going to have to knock the price down by the cost of replacing roof and gutters (and any damaged wood underneath the roofing) or replace the roof and gutters before someone will buy it.

If you’re staying 2 or 3 years replace the roof.  Based on your description it won’t pass a home inspection so potential buyers are going to want it replaced or a sizable reduction in price.  They also won’t be able to get homeowners insurance which they need proof of at settlement.  

Honestly, I would it whether you are moving now or in a few years. It has to be done. If you choose to do it now, you could perhaps give the new buyers a 'credit' and let them get it done. But either way, you are going to have to put out some money at some point. Why drag it out?

I would replace the roof now. You would have to reduce the price when you sell or give the buyers a credit to replace the roof. Dealing with that headache could also deter potential buyers. You also run the risk of more damage due to leaks in the next couple years.

if the market is strong and it's a seller's market, i would not do any huge home repairs.  there will be plenty enough buyers who will buy the house as-is.  however, if it's something vital like the roof, electrical, or plumbing, i would do what is necessary to get it to the point of sale.

I would not fix the roof.  You will have to declare the gutter issue since you are aware of it (or maybe that is just a California requirement.  I had to list anything that I was aware of in the house and in the neighborhood, which was weird). The buyer will have their inspector look over the home and will probably list roof replacement if it is that bad.  Or if they feel it will hold for another five or ten years without leaking, they will note that too.  Then the buyer will try to negotiate a reduction in price or a credit to have things fixed that need it.  

I had the wood shingle roof that was ruled out after I had been there for a number of years.  Then I got lucky.  We had a really bad storm and my roof was quite damaged in it.  Since we couldn’t just fix it with the same wood shingles, insurance paid for replacing it with those asphalt tiles instead.  I got a 40 year roof for free.

I know what you mean about being attached to your home, but it being too much for you to take care of.  That is why I sold my place after living in it for 44 years.  I think I did a great job of taking care of the house myself for all but 4 of those years when I was married, but my health deteriorated to where I needed to downsize.  I bought a smaller single story place, but it is rough going, unpacking and trying to set aside all of the stuff that I do it need any longer.  My advice is get rid of stuff before you move.  I got rid of some, but certainly not enough.

I think @fuzzymutt has a very good point. In our area, a house as you describe would potentially be a tear down and the money spent on replacing the roof would be a waste. Hard as it is, talk with a good realtor about realistic expectations for your home. If it doesn't make financial sense to stay for another 2 or 3 years, you can save yourself a lot of grief and possibly some money by selling sooner rather than later. It doesn't hurt to get more information. You can always revert to your plan to stay put for a while, but make decisions from a place of fuller information. I mean, every pea here has useful input, but none of us know your specific location and house and market. So talk to someone, or even a couple of different realtors, who really know your market.

Is it possible to replace with with traditional shingles or tin if they are less expensive than cedar shakes? I’d be worried about possible damage to the trusses in your roof if you delay too long

Do you have storms with the rain? I’d have my insurance company make an inspection before doing anything.

A 32 year old roof here (north Texas) would be an anomaly and would likely have damage covered by homeowners. They might not cover all costs but every bit helps. The insurance inspectors usually have decent contractors to recommend.

I am not a realtor; but I agree to replace the roof and gutters. The last thing that you want in your house is black mold. I know someone who didn’t know that they had a leak from their second floor air conditioner and the water leaked throughout the walls in several rooms. There is mold everywhere and the whole house has to be redone. You do not want to have to deal with it.