The level of workmanship is of a handyman quality level so could certainly use further improving.Below is a list of possible improvements/ upgrades I could make to the unit and I would love any advice as to what improvements have provided the best return on investment in terms of commanding higher rents.

I would only do this if the dogs have shown viciousness, have destroyed property, or defecate in unauthorized areas (most service dogs are trained to defecate on command). 

However, if the market commands a higher rental amount then you are justified in the increase.

This shows that the dog has been tested by official evaluators that the dog not only knows basic commands, but that he/she reacts calmly to situations such as people carrying objects, other dogs, walking through crowds, etc.

Dobermans and German Shepherds are in the middle ground—most are very tractable, but they have been bred to bite people on command, so they do bite more than breeds that weren’t. 

They are not interested in that and I’m telling them no based on their arrogance and command that I am going to provide their bail out.

The portion of the property was the "lookout" of Lookout Drive, a piece of land with a commanding view.

The challenge of raising other people up and helping them is rewarding on an internal level which commands motivation from within to achieve goals at a larger level. 

Each time you analyze a deal, you have to first understand what can be commanded in your market, and then look at what the property is now, and then what you might spend to make it better, and finally if making all those repairs was profitable.

@Jonathan S. unless this is deal of the year or something I'd say you should be commanding market rate at the very least or walk away or at least threaten to do so.