Awkward, meh.

But I don't really fear conversations or awkward moments.

(I could see it being appreciated OR feeling awkward/unwanted by a tenant/neighbor.)7.

However I feel awkward when I go to events and people ask me for my business card and I tell them to check me out on LinkedIn or to got to my website.

I really really like the sales guy a lot, and i could tell it was awkward for him trying to convince me. i know its his boss telling him what to say.

@Dennis Cronk, it's kind of an awkward phrasing but I think what you are describing is the sale of a $140K asset and using a 1031 exchange to purchase a $300K asset using all $60K of cash proceeds as the down payment.  

It's awkward.

You could have a property manager or pretend as if you don't own the home if you don't want the awkwardness of asking for late rent.

He is renovating a property and moving his air mattress around the empty units, which may be awkward; but they are OUR empty units.

But it comes at a cost, and at some point you reach an awkward stage where it's too much work to do on the side, but it doesn't provide enough income to replace your job.If you're willing to do the hard work and sacrifice a few years, you can build up a pretty nice nest egg to do other, truly passive, investing.