Not sure if I should gut it all and redo every single aspect or try to preserve some.

At least then hopefully with flat rents if they decide to not renew the option period with rental increases then the area likely will have higher rents per ft by then to release to the second generational tenant thus preserving the investors initial investment and then some.      

Well, neither does making a tenant responsible for property preservation of your asset.

Or Preserve the eventual financing opportunity?

I've paid those people lots of money over the years, while preserving my personal cash for other things.Be sure to learn before trying to earn.

There is no HOA but a Jonathan Association because the property is located in a 220 acre preserve type of setting, with trials, a lake, woods/farmland etc and it borders Hazeltine Golf course. 

Heck, most condos in the East Bay aren't even FHA approved, and that has a much wider set of potential buyers to drive up / preserve condo property values.

The best solution is for you to quickly find a job in the same field to preserve your work history.

As you can see from the pictures, we preserve the Spanish revival charm and added the espresso and cream colors to emphasize it.

Another place that I actually store some of my money to keep it working for me is the American Homeowner Preservation Servicing Fund (google it).