Sell vs Refi and Rent Current Primary Residence

[RJ Skellie]

Hello!  I am new to the bigger pockets forum but have been listening to the podcasts the last few months. I am in the "where do I take the first step" over analyzing phase. My end goal is to get into buy and hold investments (multi family and larger projects as my experience and network evolves)

My immediate question is how do I analyze selling my current home (bought high in '05) vs remodeling and holding or refi and renting? The rental calculator seemed to be geared toward buying vs currently owned homes

I paid 405,000 w 20% down in '05 and then upgraded all of the bathrooms, exterior, ceilings, fence and landscaping, plumbing, new roof...aesthetics basically.  I have comps that put me between 425-465k today.

Is it worth looking into a refi (im at 4.87 now) to create a lower monthly payment to rent?

Is adding square footage or remodeling throwing more money at an upside down investment?

I live in a historic, highly desirable family neighborhood near downtown Orlando.