Also, just awkward all around. 

Right, I don’t want to put him or myself in an awkward situation.  

Do you think I should bring a note pad or would that be wierd/awkward?

We had some good laughs.Not sure what was funnier, the fact that our son found it and that made for an awkward conversation because our 9 year old daughter didn't get why we were laughing (fortunately she didn't see the cover), or the fact that an elderly couple lived there.Then, later that day, we sat across from the lady (daughter of the couple) that was at closing to sell the home. 

Otherwise, you'd have to hand over your personal records and show which income/expenses are attributed to the investment property --- potentiall awkward to say the least.Also, don't forget that all but one conforming residential loan requires owner-occupation. 

There were less-than-neutral paint colors throughout the home, awkward kitchen cabinets, and neglected yard care to name a few things.

4) It may be awkward since you already live with these 4 roommates, but 100% make sure you get them on a lease.

No pitching or awkwardness..

But it makes things awkward when you pursue people to slap the "mentor" label on. 

Never lease to someone you can't evict or someone that would/could make Thanksgiving gatherings and family reunions awkward.