@Charlie Brown, I'm not super familiar with your market specifically but I think this strategy works anywhere:- Find a boutique, niche, ideally aging broker/brokerage in your market, and start adding value. 

Any guesses if this is the good rent for this property ?  Last tenant was paying $2300 but now I am clearly struggling to lease it even at $1900 (reduced from $1950 just yesterday)https://www.zillow.com/homedetails/23...

At least with a Conventional loan, where there will not be any prepayment penalty, or any issue with having a 2nd lien behind it.Strategically, if you are going to keep this property and want to get a heloc, then ideally you should refinance BEFORE getting the heloc.

Ideally I will be using a 5% conventional loan and will be funding the DP+ closing costs myself.

Depending on the exact location of your duplex, this could be an ideal opportunity to rent by the room, particularly given the area's demand from hospital systems and Case Western Reserve University students who are always on the lookout for housing.

Half are to repeat customers or to people staying 6+ months and paying every week.

You shared your XML file to check compatibility, and I confirmed that it's something we could work with.However, I want to clarify that we never indicated we had begun any custom integration work for you or your team.

Ideally I have skin in all three options for buying and holding as well as BRRRR down the road (diversifying).

That then presents the opportunity to convert the building to a condo which could be more ideal. 

Looks like a good number of you pay monthly, which would be most ideal for me as well.