@Michael James Ha I hear you I work 3rd shift at Crozer.  

Try telling the nurse who takes the early shift on the weekend that it's awesome to host a high school football game.

If so, and the pilings have shifted and are leaning, the house will need to be jacked-up slightly and the pilings replaced.

I actually work the afternoon shift 3 to 11 what time you guys usually meet?

Further, if your girlfriend is about to be your wife, you may need a mindset shift and stop charging her rent, and instead pool your resources.

you will have constant repairs. and the property is pretty illiquid if the market shifts, or you need out for some reason.

Local code and building costs are going to be a factor either way.What they need to determine when you add a "Story" to the house is if the foundation can support the extra weight.Here in New England, we have a lot of stone foundations and concern here is that they will shift under the weight, so the solution is to add pilings to support the house and assist the foundation.

Not sure how your shifts work at the fire station.

Financing wise you would be farther ahead to shift your investment plans now rather than later to insure a higher chance of success.

I'm attempting to create software that streamlines and simplifies the process of property management (want my app to be intuitive and not overly complex like many software solutions out there).