Lots of people market to these types of people which brings up the question "how will you get past all the filters to block people like you?"

All of this training will easily translate into your investing as well. 

Maybe doing it in a way, that this can easily be utilized in a different way, if someone doesn't have dogs, i.e. designing the bath in such a way that it can also be used as sink for laundry etc

Unless you are going after a value add type property where you can increase NOI and force equity etc.If you buy a business you can hit 75,000 pre-tax easily but you have a job at that point.

I'm currently on round 2 filtering and narrowing down the field with some preliminary questions like "have you been convicted of any felonies" type stuff.I'm not at the point when I'm ready to reach out and call a couple of these handymen to interview them.What questions would you ask?

.- keep in mind that things like spices, towels, sheets, tp, paper towels, propane for bbq's, cleaning supplies, coffee filters, soap, have to be kept up to date, clean and refilled when you have weekly renters. 

Property is in MD, Contractor primary does business in Northern VA, (So it is out of state, but the DMV area is easily connected and not uncommon for people/contractors to live/work in one state and commute to the other)I found their Web page online after several searches.  

Just my two cents.....I would recommend that you write down the necessary tasks in your business that 1) you like the least, 2) make you the least amount of money for your time, 3) do not negatively impact your competitive advantage if outsourced, 4) are easily transferrable and teachable to others, and 5) would free up your time to work on more profitable tasks.

It comes back in on the tenant's cloths.I don't smoke, don't like cigarette smoke, and I like to pick those battles with my rules that I can easily win.

The deed should be easily accessible at your local courthouse or pva office.Hope this helps.