Sometimes, this little gesture by you will turn into a big deal to your tenant and she will think that you are gold for being understanding.  

Keep in mind that many people contribute here on BP strictly as a goodwill gesture - even if you don't appreciate the input, when you ask for input here on a public forum you will get all sorts of commentary, good and bad, wanted and unwanted ...

Many will stay longer term if you provide a small discount on rent (like even just $10 per mo as a gesture) or if you simply agree to not raise rents. 

That's always a nice gesture.

Or do you do it more as a nice gesture without seeing a financial benefit?

Or even "bribe" them a little with some nice gesture so make them feel "guilty" to complain. 

If they have had to use laundromats for 2 weeks due to not being able to use the appliance, it would be a good-will gesture to offer a small credit, $50 or $75, to cover their added expense, not to mention the inconvenience of them having to haul it all there and back.  

It's a nice gesture and I think it sets the booking off to a good start and more likely to result wit a good review. 

The roof I may do IF you could show that it is end of service life, but newer architectural shingles can last 30 years, so a 20 y/o roof doesn't necessarily need a replacement just because it is 'older'...actually the only one I might do because its easy and low cost is the caulking, but even that would just be a token gesture.

For a great tenant, I would've probably gave her $100 a month as a goodwill gesture but she was a not so good inherited tenant.