The rental property itself provides the tax benefits and not necessarily the entity structure.Depreciation should wipe out your cash-flow from being taxed, especially given the high prices of properties right now.You should have your tax returns reviewed if your properties are reporting positive taxable income.

But in the right areas if you have one or two good STRs it's better than a government pension.

Just find the right RE agent who is a clone of you. 

You have to give more weightage/compromise in one over the others, to find the right home.

You definitely do not need coaching on anything right now because you don't want to pay someone to make your decision for you.

I think you left out a key piece of info.

Your analysis is right on track and  @Don Konipol provides some great insights on getting the most benefits our both strategies.  

It's great that you already purchased your first investment and have plans in mind for the future. 28269 is a good area code for MTR right now.

Market rate right now is $1200/mo and with renovations (quoted 60-75k in labor) it's hard to say because there aren't much data points, but I think I could fetch $1500-1600/mo.

Call your county clerk of court and they can lead you in the right direction.