I understand the mortgage rates are lower for second home compared to investment property.If I decide to rent this property in the future for any reasons (airbnb or leased), is that illegal?

I also don't want to spend time looking for lease holders every now and then.

if he has been a good tenant as you described.. would it not be fair to let him know your not going to re do the lease ?

I would like to begin my investing here sometime next year with a "househack" after my apartment lease is up.

Do they have a lease?

I noticed a lot post say I need a LOI, Lease and separate Option for the Seller.

Aside from being responsive and knowledgeable, she is also an experienced landlord and property manager and an expert in lease/purchase and owner financing.

If you don't have the network, I would ask the seller if they are interested in a lease-option.

I'm not interested in Windsor, but am really curious about formulas to run student rentals, and how people work leasing agreements, bylaws, etc. 

Trying to figure out what I need to do as LL - going to up my insurance,  what clauses should go in the lease?