They were all happy and smiling and even made some additional exterior improvements to the property.

On the exterior, there's mold growing up the entire left side almost to the roof and up 3-4 ft in the front of the house.

Any suggestions on how, specifically, to improve the exterior and interior appearance of these duplexes would be hugely appreciated. 

If homes were already mortgaged and were cash flow positive at the time, despite losing considerable equity and maybe no longer being able to leverage any of that equity (or lack thereof) and thereby significantly slowing expansion plans for a few short years, did the collapse of home pricing pose a significant risk or financial set back to you in other forms such as loans being called due (particularly Private money or hard money loans as opposed to conventional), were you forced to sell properties for a significant loss for some reason that I am not understanding or seeing, were rents considerably affected in the downward direction for a short period of time, or where there other significant financial set backs you encountered as a result of the collapse of housing values that may not be easily identifiable to a newbie such as myself?  

In fact I am still learning but I have a much more sophisticated outlook now based on my real world experience as opposed to anything I learned in a system.

Each interior plates is connected with a steel cord to an exterior plate, and it keeps the wall from shifting/bowing any further. 

The flooring is only needing urethane and the bathrooms to put back original with claw feet tubs and period things should run 5 each as I am an experienced do it myself person.Here in Atlanta I bought and 8000 square foot home in grant park 709 Cherokee over looking the park it had not been lived in since the 40s I had to remove all the lathe exterior and all electric and rebuild it completely I did most all this by myself and sold it close to 900k paid 320 renovation was around 120.

Or alternatively, can I ask for an additional security deposit to include him on the lease and include an addendum that any fees from the HOA need to be paid out of pocket as opposed to being deducted from their security deposit?

Not sure whether or not it's because I'm getting prices during summer when everybody is getting trees cut down.2) Can anyone recommend a good painting company/crew for large exterior projects?  

Rent increases are annual regardless of the lease in most jurisdictions.Vacancies are at the control of the tenant with a term lease, with a M2M tenants are far more communicative with the landlord as opposed to informing them they are breaking their  lease at the last moment.Good tenants have no issues with a M2M where as bad tenants will be reluctant to sign a M2M.