No matter what they recommend, get feedback from an external source on whether that makes sense for your situation.

While it is entirely possible someone can end up with no money and bad credit due to external forces (medical, loss of job, etc.), it is much more likely that inability to control spending and disregard for the sanctity of credit payment promises is the reason for their predicament.  

Currently we are interested in a 3-unit property that requires an external fire escape to be built in order to make it code compliant.

Your intent was to hold and an external force is changing that intent. 

This is best done externally ... which also happens to be the most expensive option.  

All the while utilizing external capital for the flipping side of the business. 2019 I would like to have two rental properties and flip at least 1 if not 2 additional properties.

If it is external, and doesn't come from a deep passion within yourself first, regardless of your family history and your wife's opinion, you should take a step back, and really focus on finding the motivation deep within yourself.

Too often, we're focused on external aspects of "accomplishment" and "wealth", and assume that if we're not externally succeeding, then we're failing miserably at life. 

Main house has poorly updated external wiring, poorly updated external covering (basically terrible build on an expansion) and a few rotted out wooden structure beams below the house.GOOD NEWS:roofing and foundations are solid.

Or additional lattice that may block out more of the cemetery but local restrictions may prevent such things being built too high.Such an external obsolescence will affect the ARV of the property so it must be budgeted for.