"How to Improve Your Marriage Without Talking About It" goes into this. I believe they give the example where there was a broken step that had been on the Honeydo list forever. Eventually the W just told the H she was going to fix it, asked where the tools were etc. She started to fix it and he came out to observe and just ended up taking over and doing a good job of it. I believe their point was that's a better approach than nagging, which doesn't seem to be an issue for you.

It may work in this example too. Tell H you plan to fix the shingle, ask him what tools and materials you'll need. Tell him you're going to go for it on Sunday or something. If he chooses to jump on it before then great. If Sunday rolls around and he hasn't done anything, then feel free to address it however you want in terms of fixing it yourself.

In terms of setting expectations, if W asks me to fix something and I can tell she just doesn't care that much about it, I'm a lot less motivated than if it's something that's really bothering her. If I know it's important, I'm more likely to jump on it.

Accuray


Married 18, Together 20, Now Divorced
M: 48, W: 50, D: 18, S: 16, D: 12
Bomb Dropped (EA, D): 7/13/11
Start Reconcile: 8/15/11
Bomb Dropped (EA, D): 5/1/2014 (Divorced)
In a New Relationship: 3/2015