My initial instinct is to make sure you understand the occupancy expectations for residential but especially the commercial risk portion when underwriting.

Looking to do a complete gut, new roof etc.

The current owners gutted the inside down to the support walls.

No guts, no glory. 

Autophagy kicks in and rids the body of the old cells etc. most of your immune system is in your gut so if you heal the gut, you keep your immune system up.

I'm trying to evaluate if we should keep the property or sell it/1031 exchange into another investment, but I'm struggling to figure out how to do the analysis.Initial Purchase: $65,000 (Cash)Estimated market value: $250-270k - We'd clear $200-250k if we sold.Current Rental Income (after expenses): ~$1,417My gut tells me that we can leverage the proceeds into higher cash flowing investments, but I don't know how to do the math.

Put ~$35k into it and fully gut-rehabbed it (mostly ourselves) to make it an awesome home at ~$500/month mortgage.

First of all, go with your gut. 

It seems like you have done as much due diligence as you can so I think if you're comfortable with it I would go with you gut

-Multis or single-family homes-Full-guts, cosmetics or buy n holds-Suburbs vs city-Cash vs hard moneySincerely,Your neighborhood investor-friendly Real Estate Agent