Post '08' people had the luxury to analyze for "cheap" vs the pre-'08' pricing and feel a sense of security in there current price acquisitions. 

I am subletting a property that I am planning on purchasing the set up where instead of any type of security deposit I am re-having the property which is necessary before I rent it out.I will have about $20,000 in expenses all before I purchased the property.

It depends on a lot of factors; primarily the local jurisdiction rules that may limit lease changes (in Portland/Oregon rent, security deposit, screening fees, an no-cause evictions are heavily regulated).

Even with trump's aggressive plans for mass deportation and border security, I also have to think long term about future presidents' agendas towards border control too, and anticipate potential presidents being more loose on border security.

If the agent is doing the marketing, finding the potential buyers and possibly working with other agents to help you secure a deal then I would still charge 2.5% for my listing services and 2.5% to any buyer's agent. 

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

What do you do to ensure that the tenant is responsible for security deposit disputes since that is the largest reason for owner lawsuitsHow familiar are you with the newly changed laws that can affect you the owner if they are not used correctly?.

I did the right thing by asking for the security deposit and first month of rent before handing the keys.For the next two months, she has been a nightmare.

Best approach is to have your "team" set, before going out to secure properties. 

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.