Brief updates on status: one unit failed its last inspection for three more unresolved items (I was wrong about it passing in earlier post). 

Now I have to deal with the City of Chicago myself, with a judgement against my name.Dealing with these guys has be an excruciating experience; their tenant sourcing and property marketing efforts are atrocious; they don’t respond on time, I had to hound them repeatedly over the 4+ years, checking in on the status of my property and why it was not being leased or sold.

Jason,Once the entity gets "dealer status", then everything transacted can be classified that way.

Owners & tenants should be able to log in 24/7/365 to check on status of issues.5) Do they provide professional monthly Owner Statements every month, or are they using cobbled together Word, Excel, Google Sheets or Docs forms?

Once your loans are over 1M you can get into agency debt (fannie/freddie) or CMBS with non-recourse loans that have longer terms.Note, you might be eligible for significant tax advantages via RE professional status if your wife manages the property (with help from you). 

Well, one reason the purchase the insurance product is that there’s a deferred tax advantage, as the lobbyists for insurance companies have “persuaded” politicians to grant any investment product having a minimal of insurance attached tax advantaged status.  

This way, you could use some of the cashflow to help pay down the student loans (those student loans are just plain evil), and hopefully see some equity gains over the next several years.I think the answer to your question here can be varied, as this also depends on your credit situation, current job status, income, willingness to get out of debt, real estate market, etc.Hope this helps!

And, in my opinion, 4 properties is still "newbie status".

This hazy, fog over the short term status of the interest rates and the housing markets across the US are making lenders pucker up tighter than every before. 

If you are able to get REPS status, that would help tremendously.