You most likely will not have to accept that person as there is an incredibly high correlation of a repeat offense after a first one.

I have had too many friends who were absolutely getting married, no chance of separating, it's going to happen, you can take that to the bank, it's offensive that you would even suggest such a thing! 

That said you are an existing tenant that is a one off company (No offense) so you really have no leverage over him.

This gives renters many reasons to book my house.I just had an inquiry from a highly ranked freshman offensive lineman's parents.

Thanks in advance Just to put a name on the situation, the road you are going down right now is called "mortgage fraud" and I believe its a federal offense, unless I'm mistaken.You signed a contract that said "I will live here for 12 months" and now you are trying to NOT live there for 12 months.

The percentage of time an apartment is rented as an STR is totally irrelevant (no offense everyone).

(still aren't sure if we'll flip or hold).I am trying to structure an offer that, both, makes our investment worth the return AND isn't offensive to this retired gentleman and his wife. 

If it is not the case, I might hew closer to James' recommendation but with a bit more tact (no offense). 

No offense and I've seen worse but dude the decor is god awful.

. - You're a new lender and don't know what you're doing yet (no offense meant, just pointing it out because this more experienced borrower could potentially take advantage of that)- The information a couple posts above, which you agreed with, about the borrower taking care of having the loan documents prepared is not correct.