Find a good inspector that is trusted by professionals in your area and get a good pulse on the effective life of your big ticket items (Roof, HVAC, HW heater, etc.) and calculate out how much each will cost to replace, then do the math backwards for what you need to put aside for CAPex and maintenance. 

With FHA loans, the mortgage insurance is higher and will remain for the life of the loan.If you are married, best route for your plan would be to use a HomePossible, then FHA, then have your spouse do a HomePossible, then FHA.

Documenting and pushing concerns raised over health and safety issues is also a classic leverage-move played by scam artist tenants.I'm not saying the tenant's concern is unfounded, but tenants asking for over-the-top precautions is going to add substantially to your costs and timeline.    

If the property has any health or safety hazards, VA will require that you fix them before moving in. 

To make everyone's life easier I definitely feel as if investing in the lines is the right thing to do.

A major roadblock to this, however, seems to be health insurance. 

Just ask for them to put a ceiling on how much the loan can adjust for the life of the loan and how much it can jump each adjustment. 

I am new to real estate myself, but it has been in my family and around me all my life.

I could't think of it for the life of me.

Jacksonville is the biggest city in the US, land wise, so even my sister who has lived there all of her adult life (20 years now) does not know all of the areas.