Pick the best applicant and if he is the one hope it does not cost you a friend down the road when they turn out to be a terrible tenant you are forced to evict.There is absolutely no tolerance in this business for emotions, compassion or "friends".This.Have them apply and be screened like everyone else.If things go south and they don't pay or damage the place, things get awkward fast. 

I may have confirmation bias here, but I'd much rather take my time looking through a vacant property than rush through because tenants are home and it's awkward. 

Some find it awkward to be present, others (maybe two tenants ever) have felt they must be present to guard their stuff. 

I'm trying to figure out if it would be worth keeping for myself to rent out with the awkward layout (as I do NOT have the desire or experience to move walls or add bathrooms). 

Explain your situation without making excuses, own up to the mistake, and promise to pay all that is owed plus any late fees.The more you avoid the awkward situation and make excuses, the more likely your landlord will react adversely.

I bought near the peak of the first housing bubble,  but fast forward 11 years and that property is mostly paid off, its probably worth 50% more than what I paid (after being worth less than what I paid for 6 or 7 years) and everything is renovated, and the rents are nearing double what they were when I bought. unless you are going to budget for a PM,   having one property in bremerton and the other in everett sounds like an awkward situation involving a lot of boat rides and sitting in traffic.  

Personally I don't think that I would ask for a loan from him as that can get sticky/awkward.

They do have a train station but it's in a bit of an awkward location.  

It was a 2/2 with a bunch of awkward space.

The landlord seems nice just a bit awkward at times, but we learn to deal with him, but somewhere down the line maybe 3-5 years ago he started harassing us.He started throwing some of his trash in our garbage bin.