I just don't want to be put in an awkward position or put someone else in an awkward position because of my ignorance.Thanks! 

I just hate that awkward moment.

Also look at things that may be detractors, like the neighborhood, or awkward layout, or tight hallways that will make moving furniture difficult, etc.

Houses pre-1900 often have layouts that are awkward by today's standards, and that would be my biggest concern about resale.

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 was a bit awkward but it worked.

@Alex Cornwell yea i guess letting them know on their birthday card would be awkward haha i guess it would definitely be easier being more stern with strangers

Also, this is probably silly but what is the least awkward way to get the actual lease signed?

One of the things that has really helped me has been to bring a friend or my husband along, it helps boost my confidence because I have someone to catch me in case the conversation becomes awkward.