@William Silva your ideal start might be to pinpoint a few markets with lower barrier to entry as others have mentioned, then, find someone local to that market that you pair well with and do a smaller deal.

However, if you plan on sticking the the loan and you do not anticipate rate would drop below 5.7% then option B would be the ideal route.

In my mind I think it would be ideal to wait until I get a "no-brainer" but notice as I drag my feet applicants tend to get antsy for a decision (Which I can appreciate).3.

Essentially, there must be a paid parking footprint in the area already.The ideal asset would cashflow from day one with the ability to add value via technology, operations improvements, and/or NN lease addition (or renegotiation). 

I have been actively looking primarily in the Virgin Islands and Bahamas for properties that are ideally within the budget I would like.

This would ideally include a video doorbell with an app that can manage both and see the cameras/recordings for both systems. 

Ideally, you don't want to concentrate all of your properties into a single entity in the event of a lawsuit against one because it exposes the rest of the properties to that lawsuit. 

Ideally I want the money collected to be accounted in the month I'm paying the mortgage so I can get a better sense of my monthly cashflow month over month, but that means I will need to record the draw I receive in October in September so things all line up nicely.Anyone have any thoughts on that?   

https://www.amazon.com/Westcott-Stainless-Office-6-Inch-10414/dp/B0015ZY25IThey made a movie about your insurance company, here's a link you might enjoy:  https://www.youtube.com/watch?

Compare that to my C class outside Chicago building where I deal with it almost monthly and got so stressed I ended up signing on a manager which has been a huge drag on the returns.