A good Personal Trainer can help a lot.

I am personally staying away from STR‘s and MTR‘s because of its inconsistency.

You have code enforcement issue in one of those cities and they do not know you, your life is not going to be easy meanwhile the person who has been there for 10 years and knows the inspectors families name will have a very different outcome than yours. 

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.

My 2 cents would be that since it is your personal property that your CPA is right but im far from a tax professional!

I have a personal umbrella and a commercial umbrella from State Farm.

Personally, I'd prefer to use that money payment on a fix and flip, or for marketing expenses to find that next deal.So here's what my wife and I did.

I, personally, have mixed views on this.  

Sometimes people who are comfortable managing the details of a job will hire a less skilled person to do it knowing they can get a MUCH better price and a "decent" job IF they themselves stay on top of how the work is being done.

I personally like to manage the risk and take it slow and true.