From a sales perspective, if you're married ($500k) or if single ($250k), you'd have a portion of the exclusion (%50) assuming the square footage is the same for each unit (assuming a duplex)The remainder (%50) could be 1031 exchanged into another property tax deferred. 

I'm also curious on this topic, less from a home value perspective and more from a STR or MTR strategy.  

I have three STR properties that my wife and I have self-managed but from a tax perspective we've only taken the normal depreciation the last few tax years.

I’m really conflicted and would love any advice or fresh perspectives!

There is so much for me to consider so I am grateful for your perspective! 

I don't know Fremont specifically that well, and local market drivers could change my perspective, but looking at the 3 year trend on sale price I think you'd do well to hold 6-24 months if at all possible.

If you are taking money from a C corp, generally there are better ways from a tax perspective then doing that directly to buy real estate.

I can’t wait to dive back in with a fresh perspective, connect with like-minded individuals and new opportunities!

I don't know the exact location of the property, but from my perspective a lot of former drive throughs are being replaced or no longer used, especially at former bank properties.  

@Eric Jacobs Hello, I am looking for an attorney that can assist me in giving a perspective buyer for my property a first mortgage.