Tenant asking for sublease

[Ramesh K.]

My current tenant of more than a year wants to sublease the unit. It's a 5BR SFH. He mentioned in our recent meeting that he's trying to save up to buy a house and would like to sublet the unused room (to save on his rent). I'm open to his idea given that they've been great tenants and prompt in paying rent for the past year. Current lease has restrictions that prevents subleasing without LL's written consent.

As for who to sublease, he's thinking of his military friends who would stay for a short term (3 - 6 months) after which he's planning to replace them with others.

I see a lot of posts here in BP where the current tenant wants to move out or terminate lease early in which case transferring or finding a replacement tenant makes sense. However in this case, my tenant is capable of paying the rent and he's more likely to stay or extend the lease for another year if I allow him to sublease. Is anyone here doing anything similar?

1) Should I not entertain the idea at all? Would it turn out to be a huge headache?

2) If I do allow him to sublease, I'm definitely planning to at least do a background check on the sub-tenants and approve them based on that. Would it better to also add them each time to the lease as occupant(s) or leave them out of the lease. He says he's capable of continuing to pay the rent by himself.

3) Should I write an addendum that restricts number of occupants, make the sub-tenants agree to the terms of the original lease, etc. What about additional wear and tear? Should I chalk that up as operating expense or increase rent to cover for that?

Thanks in advance for your input.