Multiple Offers on the Same House at the Same Time

[Robert Fisher]

I had about 4-5 hours of travel in the car today, so I don't remember which podcast (of the 4-5 I listened to between the OG Pod and the Money Pod) this concept came from exactly, so forgive me for not posting under a show discussion.

But the concept of making multiple offers on the same property at the same time was something I hadn't heard of before.  It really jumped out to me because my wife and I are going to look at a potential new personal home.  The owner has had some health issues and has let the place get rundown in general but also by tenants.  But the place has serious potential and even has a separate in-law suite in the basement that could be a 1 bed apartment or Airbnb so we can get in on house hacking mania.  I mean it is a diamond in the ROUGH.  Deep rough.

The owner currently has it as for sale by owner and told our agent that he will probably list with an agent have his tenants move out next week and he does some paint and other little fixes.  I'm hoping to cut him off at the pass (assuming we like it enough to make an offer) and take that piece off his plate as more motivation.

I say all that to ask this:  While the podcast mentioned this strategy, I don't remember them giving any examples.  What are some potential ways you could make multiple offers on the same piece?  This idea jumped out to me because I was debating between offering X amount and taking we will take it as is with faster close or offering Y, with full inspection and longer close.  Now I'm thinking, why not both?  

Has anybody else done this or have any advice on how to structure these types of multiple offers?