Is there a specific reason why you are wanting to obtain this information 6 months prior to the expiration of the current lease term?

Really depends on the scenario in terms of property value, cash flow, credit, and leverage. 

Sometimes, having a reliable tenant stick around long-term is more valuable than pushing for an extra $100 a month.

It's usually used for short term purposes.

On the other hand if you feel the stock market is going to under perform the 6.8% (knowing that the average long term gain on the stock market is 7%) then you might consider paying off the notes more. 

Yes, you can ask them to be out by 10/29, but if they don't leave what will it cost you in terms of eviction costs, lost rent, damages, etc.2.

I own couple of single home rentals in Tampa Florida and have always wanted to transition from long term to short term rentals.

Personal readiness includes long-term plans, maturity, and market conditions.

Zero cash flow translates to negative cash flow in the short term because you have to maintain it.  

In my state, rentals less than 30 days are not regulated by the Real Estate commission.I don't think any of these short-term rental platforms explicitly prohibit arbitrage, but I wish they would.