And frankly, some older buildings are aesthetically more pleasing that much of what has been built in more recent decades.

And everything that goes with it - including refinancing for "hold / rent" strategy.Evaluate "upgrading" primary residence to take advantage of no capital gains (lived there over 2 years) - this will also put is in a good school district which is a must for the wife.Increase number of rental units while maintaining strict guidelines on price, aesthetics, and LOCATION!

This way the two will work together creating a higher quality finished product and I will have the ability to make the necessary energy efficiency and aesthetic upgrades to the older portions of the structure.

If you are confident in your ability to come up with a workable/financeable plan that meets the group's goals for location, cost and aesthetics and the local political/planning goals then you might be able to bring this to fruition. 

Plus, with typed letters, it looks better to have a logo or photo included, thus incorporating your professional title in a more functional and aesthetically pleasing manor.

How quickly can you make a decision on location, numbers, then aesthetics?

Paint, wife provided a lot of labor to the aesthetic appeal on the inside.

In California, warranty of habitability generally does include broken windows.In any case, I suggest making a judgement call to the aesthetics of the property as well as any potential liability of not repairing a window that you are aware is cracked.

Regarding getting the most bang for your buck with the aesthetic parts of the renovation. 

This is a C-level rental house, so cost wins over aesthetics.