My general idea was if I win a house at auction, to go to the residence (still have previous homeowners there), try to connect with them in what is a kinda awkward situation and see if me paying them say 1000 dollars and paying for professional movers to move them in exchange for them not intentionally damaging the place makes sense. 

Since I don't want awkward Thanksgiving dinners, I find myself having to either guess what is in her best interests or push her towards making decisions.  

Super awkward!

If the new owners have an issue, will that make things awkward?  

@Julien Plouffe Your question hits home for me because I'm looking at several properties in the awkward 20-80 unit range.

@Vandan Mehta, as an agent it can be awkward to represent both the buyer and the seller as a dual agent but only because sometimes the clients don't understand what limits that places on the relationship.

I was more unsure if it would be awkward to ask them for a referral and then they say “oh I can help you!”

Depending on your strategy, sticking to 4 units may be a good idea since the 5-15 unit range is an awkward asset-class... 

Hi Julia, We have a property manager too, kind of awkward timing as we were literally switching when we got this bill.

For instance, I bought a place that is a fantastic rental (cashflows $1,000/mo), but it has a staircase awkwardly placed right inside the main entrance.