I am lowering the price this week, but am just curious on how often it should be reduced if I'm not finding anyone in the medium term rental world? 

It sounds like the ONLY benefit in this deal is the 0% carry-back and you are trading that for a reduced rental rate renting the property back to the family member.

However if you want to generate more cash flow putting 15% down will help you because not only is it a lower montly payment but when you hit 20% equity they will remove your PMI.If you put down 5% I would stronly encourage you living in the Airbnb if possible and renting out the home so you can generate even more incomeIf you look at it like this it'll helpMonthly payment < Potential income + current rentIf you can move and reduce your cost of living that is always great at the bare minimum they should equal each other in my opinion because at least you'll have equity if the market you are choosing is a strong equity market.

@Greg Devlin - in addition to Scott's advice, have you considered a 1031 exchange to reduce your capital gains? 

Example: If I wanted to assign a property to another investor, would I want to try and get the tenant out of the property or should I just keep the tenant inside and just try to reduce the price?

You want the flexibility to access your money sooner.4) Tax Benefits from Real Estate: When you invest in real estate, you can take advantage of depreciation and losses to reduce your taxable income today.

Or rent for less long term.IF I can make this Lake Front property a successful 30 day furnished rental, it will allow help pay for my parents care in assisted living, and reduce the draw down on their savings (and preserve my inheritance). 

This is important because you should have an idea of which locations you'll be able to cashflow a property versus the neighborhoods where it may not be about a positive cashflow it may just be about reducing your mortgage by having tenants.Bottom line- Start your journey by researching the market before you move there so when it's time to pull the trigger you'll be making smart offers

I try to be courteous and spend tens of hours into my tax prep before I ever send them off to reduce the time and frustration of the person preparing my returns.

rather than drastically reducing the price and not profiting much?