My guess would be that a "rental" is not the right strategic play for your market.

I want to stay in the short term rental business so my intent is to use the gains to buy 2 single family homes in a cheaper home in the outskirts of the city on a strategic location.

But that's me because their ROI has been far greater than 6.16% annually over the years.In summary, I would take some of the advice from the other experienced investors in your thread and consider increasing the amortization to at least 20 years (unless you have a real strategic benefit from keeping it at 15-years) and also boosting the rents to proven market values.Please consider taking those considerations into account in your analysis and share an updated screenshot of the new numbers. 

I have an 8x4 foot advertising banner I put on the side of the bed of my dumptruck and park it in strategic locations. 

We have over 100k in funds and a strategic plan in mind.

It seems I need to do some mapping and strategizing then on how to pay off the HELOC being it’s a variable rate.

I have blinds on the windows, my outside lights are angled opposite her direction, the fire pit was strategically placed so that smoke does not blow her way, etc. 

I’m trying to figure out strategic ways to raise private money.

I own 9 doors in the area and I'm looking to grow but I want to do it in a more strategic way moving forward.

I am trying to become more strategic with my real estate portfolio.