Our realtor has informed us that they will address two lower cost items on the exterior of the home and want to provide us with a cashier's check at closing to address the other three. 

There are some partnerships that are designed by nature to be short term, so there’s not as much to lose if things don’t turn out rosy.

This can become a risk for both you and your ability to sell.As for things to talk to HOA about, beyond the permanent exterior colors/finishes, I would also ask about things like dumpsters and potentially port-o-let's that may be needed during rehab.  

Exterior PaintThe home has a concrete foundation wall that extends about 3 feet up before the siding starts.

It is one of the best examples of City Council and local registered community organizations huddling together to create restrictions intended to thwart development but here they are doing it in a manner which will leave new housing stock in the dust relative to other neighborhoods thanks to terrible design restrictions.

The design & architecture firm I work for is HQed in Sarasota.

There is a unique tax deduction in the US called a “conservation easement.”It was designed by the IRS to encourage real estate owners to make pristine land, that could be enjoyed by the public, a conservation ground, and thus un-developable.In return, the landowner could treat the act of granting a “conservation easement” as tax-deductible.

Rest assured; the process is designed to be straightforward. 

Welcome Scott,There's a ton of useful resources here on Bigger Pockets from calculators designed to show profit/loss to seasoned investors giving advice.

It's well-designed, easy to navigate, and contains a wealth of useful information.