Once it's leased, they become your tenant and if you want to sell to them, you may choose to involve the same realtor, but you may not.

They issue for them has always been getting caught between a long-term lease which isn't needed and/or a vacation rental that is just too transient. 

That's for tenant turns, unexpectedly long lease times.

Ski Leases: Looking at the short term rental policies it does not cover leases longer than 30 days, seeing as there is a market for this type of rental what are peoples experience with this for ~4 month terms, and has it worked for summer leases as well.?

The contract I could find says the following:```...together with the right of ingress and egress at all times for the purpose of mining, drilling and exploring said land for oil, gas and other minerals, and removing the same therefrom.And said above described land being now under an oil and gas lease originally executed in favor of [Oil Company], Chicago and now held by [Oil Company] it is understood and agreed that this sale is made subject to said lease, but covers and includes of all the oil royalty and gas rental or royalty due and to be paid under the terms of said lease.It is agreed and understood that of the money rentals which may be paid to extend the term within which a well may be begun under the term of said lease is to be paid to the said [purchaser], and in the event that the said above described lease for any reason becomes cancelled or forfeited, then and in that event, the lease interest and all future rental on said land, for oil, gas and mineral privileges shall be owned jointly by [owner] and wife and [purchaser] each owning & interest in all oil, gas and other mineral in and upon said land, together with interest in all future rente.This sale is made for and in consideration of the sum of Ten Dollars, cash in hand paid, the receipt of which is hereby acknowledged.To have and to hold the above described property, together with all and singular the rights and appurtenances thereto in anywise belonging unto the said [owner] heirs and assigns forever, and we do hereby bind ourselves, heirs, executors and administrator to warrant and forever defend all and singular the said property unto the said [purchaser] heir and assignee against every person whomsoever lawfully claiming or to claim the same or any part thereof

If I were to rent for 6 moths, the lease would end Feb/March time frame given its almost September now. 

A strategy we use is to offer to buy and close now and lease it back to them for free.

Just as the tenant won’t voluntarily move out before lease termination because I found a tenant willing to pay more, I won’t suffer a monetary loss because they can’t or won’t fulfill their contractural obligation.  

When there's tenants already occupying the property, there's often times different leases that were signed among the tenants.Additionally, renting by room usually sees higher tenant turnover which in turn causes more work for the PM.Other challenges to consider:- Disputes/conflicts among tenants (different personalities if a tenant doesn't know the others prior)- Occupancy limits- Splitting utilities (what if someone uses more water?)

So I have a lease from back then, but it was written for a 12-month LTR tenant.