Paint can wait. A roof should take priority. Water damage from a leaky roof can cost you a fortune.

That said, is your roof leaking? If not, then there is no reason you can’t get the paint done first if that’s what you want. Roofers won’t mess up a paint job and if they do, they should be on the hook to fix it. Painting after the fact won’t cause any harm to a roof.

I would suggest roof first. If your roof starts leaking you will have ceiling and possibly drywall damage costing even more money.

If roof leaks, more problems happen. If paint isn’t done right away….nothing really happens.

Roof first. Absolutely.
I have owned three houses in three different states and climates, and had to replace three roofs. Things like paint and/or siding can wait, definitely do roof.

Roof. Big time.

Roof. +1

Who let the rain in? Roof! Roof roof roof!

Roof. Paint can happen anytime but you don’t want to be in a bind when its the roof. When I moved into my home years ago, I moved in November. In December I noticed a bit of water damage in my closet. I wanted to paint indoors but then I thought I need the money for a new roof. Well we had a horrible winter of sleet and couldn’t get anyone to do my roof because there were so many homes losing their roofs to heavy snow and sleet. Finally by Feb I could get someone to get to my roof. There was a little more water damage but I guess the bad patch wasn’t too bad. But I freaked out for 2 months worrying that the weather was going to damage it more. New roof, and no leak for the last 14 years.

Well. Speaking as a former teenage roofer/painter, when they rip the old shingles off, it can damage parts of the house.
So. I wouldn’t want to paint it, before the roof is done.

If the company you use for the roof does a good job, I bet they paint too, or know someone who does…

I’ll just be a contrarian and say paint. (Although I really think do the roof first.

It’s the wine @Caravanfan

@Dutchess_III And whisky and beer.

As long as your roof actually needs to be replaced, I’d do that. Just be sure, because convincing people they need new roofs when they don’t is a very common scam. Some roofers will even come to “check” and actively damage your roof to prove it needs replacing.

Roof first. When building a new house it’s usually roof first if that matters to you as an example of the usual order of operations on a new build.

Roof first. It could compromise the house.

Roof.

Roof first.

Ok Thanks all. Now here comes the curve ball: I have some bare spots in the front (trim) where paint has peeled. I have a new home policy that entails a drive-by in the coming weeks. Can I fix up those spots just to get by, and come back to the main job later?

Then I will look to the roof, before tackling the whole house painting job, as long as I can do them in either order.

No leak, by the way, but there is still cause for concern. I have to get inspection and some estimates.

Yes.

You should be able to touch up. There might be a slight color mismatch, but the paint will be protecting the wood, which I think would be the concern of the insurance? That’s my guess. I don’t know exactly what they look for.

Just for the sake of variety, I say paint your roof and put shingles on your walls. ;-p