To me, offering your condolences to strangers while simultaneously trying to get their house for dirt cheap comes off as insincere, bordering on rude.

They do volume and work many different markets simultaneously. 

Recently he has become more aggressive about the subleasing of his space while he continues to run his business simultaneously.  

We are able to get a higher cap rate in Detroit compared to California while simultaneously spreading risk over multiple properties.

With that said, I am sure that there are many people making money in real estate in the tri-city area, and if you are living there anyway, you can certainly house-hack and decrease your cost of living while simultaneously growing equity in properties.

I made 2 simultaneous offers.

@Benjamin LovingerI have been successful on this for both directions (listings and purchases) and I find that posing the options simultaneously in an unbiased light is the best way.

But anyway once we finally closed, he got to work on the foundation while simultaneously working on renovations to the interior of the house...I was lucky to have a very competent contractor who worked meticulously and quickly and this was all done in 3 months time! 

Arguably, you can’t even sue to collect on a commission in this case, even if you have a signed contract.The second weakest position is being a licensed broker in the dealA middling strong/weak position is being the middleman in a double/simultaneous closing.A stronger position is to be able to take down the deal with outside financing and then “flip” it to an interested buyer.Finally, the strongest position to be in is to be able to complete the purchase yourself using only your own cash.Note that you don’t have to actually close with your own cash, or even close in your name.  

Yes it can be done and something that simplifies it would be doing a quit claim deed into the LLC that holds it, and simultaneously refinancing it into something with a new lender.