I am going through the pre licensing courses/ process now.My rough plan, as of current, is to begin flipping homes in desirable residential areas nearby and then move to flipping in the mountain/vacation setting.

Or you may be getting tired and desiring more passivity to pursue other passions.The point is that once you get these questions answered then you'll see a direction to go. 

Totally legitimate desire. 

Gaining long-term equity and having renters cover most of your mortgage is a great investment strategy, especially if your local real estate market suggests that selling may not yield the desired returns at this time.Regarding your plans to purchase a home in Ohio with a lower monthly mortgage, I would suggest exploring the local real estate market and looking for a property that suits your needs while keeping costs manageable.

@J Scott - How do you manage contractors so you get the price you need, the quality you desire and the timeline you agreed to?

With "Condo Status" comes not just increased desirability, but also higher appraisals during refinancing.

I have about $250k in equity in the home and my realtor believes if we list it we will probably get a bidding war in this market and since our neighborhood is highly desirable.

I'd personally think on lifestyle desires, plans in the next few years, etc when asking myself if this sort of thing is a right decision.

I am looking for a private lender to finance my rehab on an already owned, gutted property in a desirable neighborhood of the city (Upper Lawrenceville): demo complete, structural engineer sign-off, architect-approved design to move the stairs (which is not a small deal in Pittsburgh), and city permit.

Home is in desirable Oakmont, PA.