My goal, over the next five years, is to utilize real estate in lieu of my current hourly consulting income, by building a portfolio of rentals.  

You should consult an attorney or CPA for your specific situation.ANONYMITY: When you create the LLC, your name is recorded on the documents and published on the Secretary of State's website for all to see.

@Caryn FischerI agree with Jaron, you should definitely have a consultation with your tax accountant and/or financial planner before you do anything. 

I would also recommend reaching out to a Zoning Attorney and checking to see if they may have any additional insight as to the feasibility of obtaining a Map Amendment in this area.

Always consult with your attorney before you rely on the above information.

I would need to consult tax consultant for this however I expect to reduce my effective costs by ~$1,495/month (based on a 32% tax bracket).2.

Anyone has a recommendation for affordable yet experience designer to help with few hours of consulting to upgrade the look of   new airbnb?

Financing might be a challenge.I would recommend consulting with a attorney, loan officer, and CPA to discuss your specific situation and determine the best course of action. 

I will be obtaining half acre of family land this year.

First, most investors and owners of real estate related businesses are in one or more of the following situations1- they’re unable to duplicate their expertise that drives the ROI and they are at their personal max capacity as to time2- they’re obtaining high ROI by use of excessive leverage 3 - they’re obtaining high ROI by taking excessive risk4- they hit correct timing in the correct market, and this is not necessarily repeatable with any probabilityIn order for an investment or business to scale, we need the ROI (on a risk adjusted basis) to be sufficient to cover a PREMIUM risk adjusted return to passive investors; all expenses of managing the assets and the business, and a significant return to the “sponsor” providing compensation to him making the work, risk and time worth while.