With enough knowledge you can make a educated decision on which approach you take.My experience:I personally don't sign up for any program who take you aside during events and try to sell packages that is just blatant sales strategy.Once you sign up there is every attempt to make you sign for their programs for bookkeeping, registered agent, LLC or corp setup fee which have ridiculous even with platinum membership.Basic standard structure they suggest to take advantage of multiple deductions can be easily achieved by proper education or work with a good firm like https://wcginc.com  who is local to you.A umbrella C-crop to manage all other LLC properties and take advantage of many tax deductions that are not available with a llc, its also used to take losses up to 100K as startup expenses and dissolve the entity after few years.Few LLC entities for investing in Real Estate, etc preferably in Wyoming or Nevada ( you can find many companies online who can do this for $150 compared to anderson $1500-$3000) , they will claim they have a secret Operating agreement which is bogus.They certainly try to take advantage of tax loopholes and claim to be smart people, my view they are just taking advantage of numbers as per their own statements.

Property Manager – This is another one I really need help from the bigger pockets community in the local area.

Are you currently managing your own properties or do you have a property manager because many times a property manager can perform the work needed for it to be turnkey.

Build relationships with local agents, property managers, and contractors who specialize in investment properties.

Since your goal is getting into commercial real estate, it might make sense to start with a smaller rental property like a duplex to get experience managing an investment.

But what I will say is that he is a disastrous relationship manager.

We manage between 80 and 100 listings it varies winter to summer but the processing of manually Remitting and paying out the property taxes takes much longer than 10 min.

@Sean GammonsConsider adding a partner for the second deal to share the down payment and mortgage responsibility, keeping DTI manageable.

I'd start by talking to others who are landlords or property managers in your area.  

What's your biggest time management challenge?