I'm considering the wrap option so that this time frame could be extended and he could be free to go get a new car, house, etc... without this mortgage effecting his ability to finance.

Other one sounds like a possibility - will just be a slower turn around if you have to get the tenants out first.

This sounds like a fair fee but you maybe paying for more then you need.

If it were my lease, I'd just add language in an addendum to clearly state it was under the month-to-month provision from dates x to y, now lease term is extended to ... and all other provisions still remain in effect. 

Tenants that pay on time and would like to stay another 3-5 years that sounds great to me as a landlord.

@Melinda Francis - I know this sounds surprising but you don't have to have ALL the answers before starting. 

Dan Hey Dan, sounds like you've got a solid plan.

This is the most basic level of protection and it is not very effective, but it is still better than nothing.

It sounds like you need to evaluate your property and narrow down what it would be best suited for.

Searching for investors and properties in residential and multifamily sectors sounds like an exciting venture.