@Lisa Hall, difficult task to ask any lender to take a 2nd position on a primary residence.

The biggest advantage I have to getting started is the internet and a forum of landlords that tell you almost to a "T" what to do so you don't have the problems of landlords past. 

In low rent areas, it is my belief that the 50% rule should be allocating higher than 50% to expenses, other than the debt service, if you are hiring out the work.If you do the easy tasks yourself it will help your cash flow. 

An easy task to one is difficult and heavy to the other.

Someone who complete this task for you in 2 days give or take?

I am trying to be careful not to 'waste' anyone's time unnecessarily, so I am trying to take on the daunting task of researching for my own potential brrrr properties in areas I'm unfamiliar with.

If you have a good paying job and can afford a new loan every year then you will obviously accomplish your task much faster than someone who is broke, or worse yet in significant debt.  

I am an engineer so I use a detailed spreadsheet.I add up all my costs and these are many and subtract that from my estimated income.I look at similar properties and see what rates they are getting and how often they are booked.Excel does the math for you once you have all the numbers.Remember for a VRBO you have to pay for the utilities (don't forget cable or satellite TV and internet), consumables and furnish the place.

DISCLAIMER: I am neither an attorney nor a CPA, and I don't play one on the internet.

It does feel a little scattered and difficult to work backwards to tasks for this month, this week from that.Thanks for the insight!