I understand the benefit of having guests' contact info for myself, but in 2 years we have not had much success yet with recurring guests coming back to book directly.

I certainly wouldn't want to get into this as a recurring problem having to rent it in winter due to having one year leases expiring in winter.

I'm still trying to nail down an overall strategy that leads down the FI road, addressing key questions of cashflow, equity, scalability while reflecting my current savings and recurring earnings. 

Our management team started doing monthly recurring leases that automatically renew.  

Enter recurring charges and automatic late fees.

But the Real Estate Investor truly operates from a transactional and recurring entry and exit position in the course of months.  

Some property management softwares allow that.It may be a bothersome to keep entering depreciation expense but in quickbooks, you can set up a recurring depreciation expense so it should help you out.

The up side is appreciation and good tenants, less recurring maintenance, vacancy is very low also. 

I made the event recurring for the first four dates; we'll see how well turn out is :) Looking forward to meeting you!

@Brady Mullen Debt is used for --> Appreciating Assets and assets make you --> Money, preferably immediately and/or on a recurring basis.