And it puts your friend in an awkward position.

More like a squeaky voiced, awkward growth spurt sort of investment maturity level.

It may get hairy when I get a listing from one, who got it from the other...awkward!

If it's the office of the trustee who's managing the trust until the son comes of age, maybe you can get some more information from them to help you answer these questions without feeling awkward about taking to the son right now...

We also don't want Thanksgiving to get awkward!

I thought about trying to talk options with the owner, but felt awkward about that given that my agent was there.So I'm wondering, what would a pro do in a situation like this?

Always sucks to be the awkward one late to the party trying to play catch up, but the more information I can absorb right now the better.  

If you'd like to minimize your contacts with your tenants because it feels awkward consider using a property management company.

It's just not worth the hassle and closing costs for 35% LTV based on my investment (23% LTV based on appraisal).Rather than the typical large banks that have policies written in stone, I took some advice of the James Vermillion and the BP community to shop around to two small regional banks today.It was the most awkward experience ever.

Would be awkward if I didn't choose him since I will be seeing him every 3-4 months for dental cleanings.