Currently, asking some of my close friends to help sign a lease agreement with me.

I found a tenant who signed one year lease contract.

What a good app to keep track of leases with tenants and collected rent money each month and automatically apply late fees if they don't pay on time?  

Rent collected way under fees paid lease, extra utility charges to me, management fees, taxes, insurance,  do not even come close. 

Ideally he will be stay there for 10 months and lease the property from the new owner while he gets ready for his move. 

-I will then put in place a lease agreement between ourselves personally to the new property management LLC to lease the cottage and between the ownership entity of the other rental property to the prop management company. 

Do you have any clauses in the lease about cleanliness that they are breaking? 

You need to hire a Commercial agent to lease that for you.

The current tenants have a lease until end of January, which I will honor.

And I noticed that many of the unfurnished units were offered with a month to month lease... the kids would get cheap furniture that they didn't care about tearing up and giving away when they were done.