If you can cover that $155/month out of your personal budget and rental income from the other half of the duplex, you might decide it makes more sense to keep your first property running at a small loss for now and reap the other benefits of real estate: principle pay down, depreciation, future rent increases, etc.Especially when you look at what it'd cost you to sell it at this point. 

Ultimately you may chose to spend the maint cashflow another way and plan to use a LOC to handle issues but that expense should be counted when figuring out if the property is cashflow positive or not.

CallRail refuses to add my calls to the “Calls” app and I’m spending more time inputting data and working out bugs in Podio than getting contracts signed and Returning phone calls.

That would include you or them acting as a third party facilitating a real estate transaction between two other people.If you are only buying properties for yourself to flip or whatever, and these appointment setters are your actual W2 employees and not 1099 contractors, then you are probably OK.If you're a wholesaler and don't intend to take possession of the property, well that could be completely different.As always, I would advise spending a few bucks to talk to a real estate attorney on matters like this.

However, do bear in mind that houses that are selling for 10-15K over asking price are being sold to RETAIL buyers from sellers who could afford to spend the time and money to get the house in tip-top shape to sell and who have the luxury of waiting for the sale to close.

The first one I am managing myself because I am in the residence so there is no need to spend that money but the 2nd investment I will get a great property manager.    

Yea you could spend time looking for better deals but for me being and engineer with a day job my energy was better spent at my JOb.

Since mine were rewards credit cards I hit them all very hard to quickly reach the "minimum spend" requirements for the added rewards perks.

I would spend the effort finding another contractor and get it done.

Either spend some time studying @Amanda Han 's book on tax strategies for real estate investing, or hire a professional.