Costs a lot less to do all pad sites together versus individually. 2.  

IF that is the case full stop - yes you are paying for something called insurance but if you have a claim the company has the right to pretty much deny coverage for having the wrong type of policy.Landlord policies are higher cost but for a reason - there is a different and increased level of risk when the house is not owner occupied.Talk with your agent and get all the details sorted out. 

Lastly and before you think I am going to sell you a training program that cost thousands of dollars.  

If I got a home equity loan for Property 1 and used the proceeds as downpayment for Property 2 and then got a 2nd loan for the remaining 75% purchase price for Property 2, when I sell Property 2, can I use the Property 1 loan as part of the cost basis for computing Property 2 capital gains?

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

How do you handle challenges in a deal (unexpected costs, market shifts, etc.)?

It will likely cost you several thousand or more to rehab the home upon turnover.

One of the big benefits of buying the whole thing on a fixed rate loan is that one of your major expenses is fixed for a long period of time, including the cost of the land. 

It's costly but that's what is expected.  

Rank them from best to worst in management cost*4.