We're flip flopping between managing the property ourselves, versus having a property management company do it. 

However, they can’t do the study for a number of months and I need it quite soon.Software estimates put the amounts much lower around $50k.Any thoughts on the software versus the engineer?

If he is using leverage I would wager he will ultimately end up paying UBIT.

The code and requirements change, versus residential, is huge.

Even deeper on the growing/vineyard side, farming annual row crops versus growing perennial grapes is a vastly different business model, has much greater appreciation potential, and far different income/acre than row crop farming.

I am exploring my options for private lending versus a business loan for a new construction deal and am trying to figure out the best way to go.

Being that I am employed as well, I wasn’t sure how I could juggle doing so much at once versus working at my own pace and time wholesaling.

You may want to consider the near South Side versus the far southside.Regarding getting taking advantage of, where a property is located won't prevent getting taken advantage of.

Beware the higher tax rates in the suburbs versus the city though.

And, a whole lot of smart people choose to rent when moving to a new city versus taking the plunge and buying in a market they don't know well.