If you can hack your primary, generate enough revenue from that you can then find another property to invest in.

This would provide me the capital necessary to fund my real estate business and get it off the ground and also provide a conservative reserve for unknown expenses.Effectively, I'd be making the decision that I can actively manage my real estate portfolio in a way that will generate a return better than the stock market (index funds via 401(k)).I've been a passive index fund investor for years and the thought of decreasing my retirement account contribution is painful.

@Karen Chenaille We would love to see the screenshot of your report generated using the OwnerRez integration. 

. :)We constantly get comments about how well equipped our home is and I think it is a major driving force behind our all 5 star reviews.

I wouldn't pay $650 mo to advertise your home in TIME magazine, the sources your using should generate plenty of quality leads, I think the problem is elsewhere.Is the home nice and clean?

My strategy is to play the long game and generate marginal cashflow while I hope/wait for continued appreciation (in equity and rental rates). 

I may be wrong in assuming this but MOST agents have your best interest, it's how they generate more business by making sure you have a good experience.

They supposedly generate state-compliant rental agreements.

But I'll have to put around $27,000 down, to generate 300-400 a month, or about $4500/year.

If they are busy with Sales, which generate big commissions for them, they may not have the availability or focus that you desire, even if they have a big "team".