It just makes difficult conversations awkward.

If you are ever in this position again, I know if might feel awkward or uncomfortable, but try to have your ducks in a row and get in your offer to them sooner to give you the best chance at a deal.Now that the opportunity has passed, you need to do your homework to really narrow down the criteria it is going to take to make this property a viable investment.  

You should be upfront about it, but also remember that it makes it awkward for them too.

We ended stopping the business relationship for the benefits of the family and to avoid awkward Thanksgiving dinners.

Rehabbed the kitchen (new IKEA cabinets) and fixed the toilet/replaced sink in bathroom - the contractor who sold it put a brand new bathroom vanity in but none of the contractors must have bothered to sit on the toilet and see if it fit your knees when sitting on toilet - totally awkward and would NOT work - had to replace that brand new vanity with a small sink (no base) - grrrr.

I find it  awkward for my rentals, I have my own trades. 

The house has great space, little awkward layout that I want to fix if possible.

It was great (minus the fact I was this super awkward kid and one of the kids I had gone to middle school with was on the trip and was a bully but I digress)!

-other than it being awkward to possibly rent to a student I teach.  

That said if you are jonesing for an awkward experience, this might fit the bill : )