If the location is as great as you say then the discount for the roof aesthetics may be trivial versus the cost of a patch job.

It usually consists of must do items that are hazardous/cause liability issues (must do), should do items (which make it easier to secure a tenant, and prevent angry calls later once a tenant is moved in) and would be nice to do items (aesthetic things, like changing a shower curtain rod that is a little rusty but not broken, or getting something minor repaired).Concerning the paint and items that needed repair - the owner was in an "I'm leaving, let someone else do it" mindset.

How is the aesthetic appeal?

Using the data from the sales of those 100,000 Chicago homes, and controlling for any number of variables---location, age and quality of the house, aesthetics, whether or not the property was an investment, and so on---it turns out that a real-estate agent keeps her own home on the market an average of ten days longer and sells it for an extra 3-plus percent, or $10,000 on a $300,000 house.

If you can get a few inches even, then you could stand there and actually utilize the corner and that would be your best and most aesthetically pleasing option.

From an aesthetic point of view, I'm a fan of combining historic and modern features - too much 'antiqueyness' in a place doesn't grab me, but I also hate to see great architectural features and workmanship discarded.

And good for her if that is the case).If you're going to be in that top 1%, and have the personality disposition to do either (I do not, hate driving, weak sense of aesthetic, tell me the kitchen "feels too cold" and my response would be to turn up the thermostat), Realtors at that level out-earn loan originators. 

Of course, before you decide on a roof tear out, you should have the entire exterior and new roof blend in nicely for good aesthetics.

Personally, we did the flooring, painting, some demo, landscaping, a lot of trim work, and many of the smaller aesthetic projects (floating shelves in the guest bath and laundry room, sliding barn door, etc.) on our own which cut costs a good bit. 

I hate to see a nice counter top on some terrible looking cabinets LOL I'm a kitchen and bath designer and look at the overall aesthetic and function.