For me I build trust and so when I go see the property they trust me so feels awkward to have someone else show up.

I also get what you're saying about the awkwardness of showing the tenant the util. bill every month and asking for their portion.Still, I feel uneasy giving free rein to the tenant to use resources without any cost.

Awkward silence is golden and they tend to ramble on and get into some juicy details.

Even if there isn't anything WRONG with it that seems like an awkward relationship to have when the frist 5 minutes of it is that conversation!

It can be an awkward situation to show a property that is occupied, however, I keep it short and sweet with the current and prospective tenant during the tour and have the formal conversation outside after showing the property.

Oooh... tough awkward one.

Some people are afraid of calling back and dealing with the awkward silence as they try to figure out who this random person is and piece the puzzle together.  

Don't borrow from friends and family   It makes gatherings and holidays awkward should something go wrong. 

It is challenging enough being a landlord, you don't want to have to deal with grown adults arguing over parking.Personally I would rather not inherit tenants, but as a new investor I could see wanting to have money coming in (hopefully) from day 1.Awkward unit setups are tough to deal with as well.

It can be pretty confusing.One of the things that I decided for myself was that owning physical property in an IRA was kind of awkward and that I would prefer to use those funds for private lending.