Next, I read @Scott Trench - Set For Life, it really intrigued me even more about the benefits of house hacking a multi family property.

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.

All said, there can be numerous reasons a property is listed for an extended amount of time that have nothing to do with the physical condition of the improvements.

I was not aware of that, and it could very well be true, but because this was not something we altered during the renovation, I don't feel it's our responsibility to address it now, after the home is sold.

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

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 really believe that while an agent should be very knowledgeable about the real estate market....you should also have a great connection with that person because its going to be a fun/scary/emotional/weird/crazy/hectic time and you want to be able to ride that roller coaster with someone you generally like and can stand putting up with numerous showings and phone calls and texts.

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.