I saw him a day or so later after proposing to offer 25% less than asking price and he awkwardly cut the conversation short.  

I feel more socially awkward than ever before & I'm afraid of being thought of as weird!

The first couple of ones will slightly awkward while we figure out the direction, ongoing logistics etc..

Honestly don't recall what the carpet looked like (oops, tenants were present, felt awkward).

My main concern is that it's just awkward to say "I want to rent this property, just not to you" since she technically hasn't violated the agreement, and she is a neighbor.

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

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.  

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

If a current tenant doesn't want to live with someone you find, they'll make your house showing awkward and you'll have more vacancy.

It gave me so much experience in dealing with people, having the awkward conversations etc...