Now the city is requesting the following:1) Energy compliance documentation2) Mechanical (HVAC) Drawings3) Plumbing Drawings (Hot, cold water waste and vent. gas)4) Electrical (Complete Drawings)What kinds of people do we need to hire for these drawings and plans? 

By using solar lights for street lights, solar leasing for owners instead of only grid energy, using under ground water to water plants etc.

And becoming a "Premier" listing on VRBO with 5-star reviews etc.

In your situation, I would say this deal becomes a very poor investment after you move out (especially considering your $392 monthly cashflow, excluding the cost of your time and energy spent managing it, and perhaps some utilities expenses that may or may not have been accounted for here). 

Had I knew how to prepare for this, it would have saved me time, money and energy.

They blew the Olympics bid, the pushed away the Star Wars museum, they acted like they had the Amazon bid locked up, and I'm concerned the Obama library is headed for disaster, or Hawaii for that matter.

If that rate is enough to make deals go from good to bad, then put some energy into fixing it.

Now you know how much time, energy, money, and effort it takes to do it.

For instance, as a flipper if I wanted 40-45% profit margin then I do the calculations at the star of underwriting to see it the deal makes sense.

But it won't be pumping at the required rate to get enough volume of water upstairs before it loses its energy (heat).