I know I need to learn all local regulations, why the property is available, if the current tenants have leases, all of the financial analyses (Let me know if any of you have come across something I might not know), section 8, available grants, and possibilities to finance the deal if the numbers work.  

I would say look through your lease which you've probably already done.

I'm guessing we end the lease, contact insurance, do repairs - then relist it for rent? 

Think practical and comfortable.Lease Structure: Mid-term rentals typically run anywhere from 1 to 6 months, so having flexible lease terms is key.

Common fees will include a set-up fee, a leasing fee for each turnover or a lease renewal fee, marking up maintenance, retaining late fees, and more.

I am also considering selling the property next spring so this would be the last lease and I don't to play nice. 

For investors who own or have owned wedding or event venues, what are the typical lease terms you've leveraged?

The underwriter of your loan may want to see your current property be leased and make sure that it covers your PITI, but that will depend on the guidelines of your lender.

I recommend dropping your price (not your standards) and renting it for a shorter term to get through the winter months, then look for a one-year lease again in the spring.If money is tight, you may consider selling.

There are lots of rental management companies, and finding a good cleaner and support person is possible.