He's the numbers guy and I have experience with construction and aesthetics so we will make a good team.

Theoretically the HOA fees should be contingent upon what the HOA is providing for you (landscaping , external aesthetics and potential coverage for the unit itself)

Your short term and long term costs will be much less as the aesthetic of the floors will last much longer than a floor refurbishing.  

Made the backyard more aesthetically pleasing.

The good looking expensive one's or the really cheap but much worse looking ones or these ones that are average priced but are kind of close to the expensive ones but lack much more in aesthetic quality of which I'd rather pay a little more for the much better looks?"

While it is a legal 2 unit, it needs at least 15-20k of work to get it there.Are we making a mistake putting our aesthetic and character desires in the way?

If you will be abiding by the Secretary of the Interiors Standards for Rehabilitation, or if the review board requires certain aesthetics for the home, you may need to use specific or hard to find finishings which could be more expensive.

These would be more aesthetically pleasing and be designed for your problem.

It's partially newly updated, with some areas that could use modernization but are not aesthetically unpleasing.

Focus on the aesthetic of the property before adding bells and whistles.