This strategy is called a wraparound mortgage, beware this could cause the bank to call the note due (but most of the time if payments are made on time, they don't - But be prepared to refi or pay it off with cash if they do). 

If so, this could seriously eat into your profits and even cause you to be upside down. 

., it may be the case that investing in RE may always make him uncomfortable and cause him a lot of stress which will undoubtedly negatively impact your relationship. 

Some lender will accept transfer to a single member LLC that you own 100% some won’t.The transfer by itself is made with a warranty (or special warranty) deed as a quit claim may cause title insurance problem.In some state/counties this transfer may trigger transfer tax or reassessment of the property value for taxes.

We have a cooperative occupant who will most likely not cause any damage to the property and they get certainty of outcome and cash.

Unless it is tenant-caused which this is highly unlikely to be.Educate them about their tenant rights. 

If you feel the implications may cause you undue hardship during or after your employment ask them to revise the contract to a more amenable wording.

Hard to say how a leak could cause what you describe.

It is causing sewage issues and we would like to hold them responsible.

I of course have a SD and the lease states that it can be used to repair damage to the property caused by the tenant.