2.What is their position?

The STR has higher expenses than LTR, so this is no where near as much cash flow as getting $15K/month for an LTR but it is significant positive cash flow.I suspect the rent as a LTR will be between $5.5K and $6K per month but we have done a rent survey yet in part because I am anticipating the LTR rent may fall due to the increased supply of LTR units. 

It's about ROI, risk, equity position, appreciation, not doors.

I have two scenarios:Pay off all my debt with the HELOC and wait for my FICO to jump to position myself better for the next property PurchaseorKeep the HELOC and have only one debt (student loan) and possibly use the rest of it for hard money as a down payment on next purchase.I plan on house hacking my next property by REFI my Duplex into a Conv. loan possibly Investment or Owner Occupied.

Commercial you will have to worry about build outs required by new leases and about how long with what kind of raises in rent you will need to do to keep the cash flow positive. 

You have positive cash flow, I would hang on to it for a few more years. 

The thinking is that even if i dont make any positive cash flow beyond the expenses as long as all the mortgage, HOA and expenses are paid by the rent i am getting that property paid off and getting equity basically at renters costs providing it is never vacant.

Here is the breakdown:1st position loan at 2/12 - $486K2nd position loan at 0/10 - $25K3rd position loan at 0/10 - $27.5KPersonal money in the deal - $30KTotals are about  - $568,500Value of the property is about $600KLooking to refinance the first loan to a lower rate and rent it out or seller finance the deal.

I'm in a position where I can leave my job and live for a bit on a pretty decent bonus.

My personal goal right now is to buy at least one positively cash flowing rental property by the end of the year in the Chicagoland area.