While this is a lot, I am looking to start with either the stable or the lodging in place and then expand. 

My research on being a landlord has reignited my interest in real estate investment.I hope to buy a property locally in the next six months and then expand to another state within a year.

If your goal is anonymity then you have to choose a state where your name is not recorded. 

I have been working with investors over the last 3 years helping them find good deals on land in desirable locations and then building a new house on it to resell.

You may be able to close and then do the 2nd mortgage afterwards, however.

My insurance agent said it’s a lot cheaper to spring for a full year policy then get a refund after you finish then to buy the short month policies.

Any time spent on your properties will provide you with invaluable experience and understanding of the asset you own.As you scale, you will hire more and more work out but until then don't be afraid to get into your investments.The picture below was a long day managing a community park we are building in one of my mobile home park communities. $50,000 job done for less than $10,000.

What if you can get in, make all those moving parts work, then they changes the regulations there? 

If it is raised wood deck, then expect it to rot and look nasty after ten years.

If that is the case then choose the area you like most, but if you are wanting to get a quicker return then I believe the Lookout Mountain lot might be better with the Paradise Valley Mall upgrade being somewhat close to that area.