If you do, you could give them an option for a month to month lease if they use you to purchase their new home.If that is not an option, I would stick to the lease end date of June 30th.

A lender may want all properties insured by the same company with the same renewal date, so you may need to adjust things and see your agent before applying for a blanket mortgage simply to know what the costs will be. 

If I let it run its course the system prices regular dates too high and it prices our peak season festival dates too low.

I let the tenant chose their rent due date and frequency such as weekly, biweekly or monthly.

Hi Wilson, I'm using Guesty for Hosts now, but's a low-end, dated solution that's, increasingly, being positioned as an on-ramp to a higher-cost Guesty for Pros upsell. 

They look in good shape but...dated.

Stay up to date with market shifts, money choices, and the best ways to fix up to make smart choices.

Any little miss wording or failure on dates can throw a 1031 out or create taxes.  

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I notice a few comments from out of state lenders/brokers that are referencing what seems like the property taxes and/or transfer taxes, not mortgage recording tax.In NYC transactions, property taxes are pro-rated and sellers + buyers pay for the portion they're responsible for (depending on the calendar schedule of the county + closing date).