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?

By completely eliminating a product that was abused and unregulated leading up to the meltdown in 2008, lenders essentially eliminated the ability for some people to obtain a type of loan that was originally designed for them.

I don't see how instructing a tenant where to park or giving tenant notice to move vehicle into designated parking is "harassment."

Possible a designate smoking spot for the tenants that smoke.

In general you cannot discriminate against families, but it is - or at least was - possible to have a building designated as adults only.  

As to ratio analysis, some approaches to an asset portfolio may apply, such as the quick asset test or maturity distribution, but they are not adaptable to real estate as they were designed to measure performance of a liquid asset, real estate is not, the approach to asset management is different in maintaining and improving and revitalization of long term assets. 

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.

We're going to physically go in 5 properties (two with our contractor, one with a designer) as well as a bunch of other properties/projects we've completed. 

There has been much research on Crime Prevention Through Environmental Design and the benefits of community working together!

I usually throw everything on the floor out, soak the place with quality enzymes designed for pet urine, and clean everything thoroughly.