Also 4th quarter of last year Packwood and county officially did discuss potentially regulating STR's by either limiting numbers or adding a tax to cover increases in local services that are needed.

I have found that this can bring it down from potentially 60 people to maybe 6-7 qualified applicants who are actually going to show up to a meeting to view the unit and then I go from there as to which 1-2 I am going to start with as far as running a background check on.

This is one of the few things Baltimore City Government actually does efficiently - probably because there aren't people in the loop.Log into your Baltimore City Department of Housing & Community Development online portal, click the "My Account" at the top and then "Permits & Docs" on the left side.

Shopping around for the best interest rate and a rep that will actually give me a call back.

Research rates for a payroll service for your employee that can handle your federal state and local employment taxes / calculations Know your federal state local and county tax requirements as well as whether you must have workman's comp for the person or not.

Obtaining competent management was an issue, I have no confidence in the service personal in the local area.  

This path makes sense because buyers will feel they are getting actual value, possibly saving them money for an real inspector if there something grossly wrong with the house.

The home is located in a Master Plan neighborhood with good schools, nice amenities, etc.My plan is to then move out of the 2nd home in a year and rent it for an actual profit and move into a new home using my wife's VA loan entitlement. 

The #1 website that has been servicing the Mid-Term Rental and monthly stay market for over a decade is MonthlyRentalsByOwner.comThey don't charge service fees (like the big sites VRBO & AirBnB), plus you get immediate direct communication with the guest.They only charge an annual subscroption up-front of $173/year per property, and that also gets you posted as well to their Snowbird website for monthly renters, www.AmericanSnowbird.com - all included in that one annual fee.

Anthony, If you haven't already join a local real estate investing club and start learning from other members who are actually investing in your area.