The 1031 Exchange process is complicated. 

Most are tied to a brokerage and focus on doing higher volume of easy transactions and aren't interested in complicated "out of the norm" sales.E-Title out of Detriot, Legacy out of Clarkston or Lighthouse out of Hastings can help you. 

We tend to over complicate things 

I am not totally against LLCs, I just think you don't need them when you are just getting started because it just complicates the transaction and I am a fan of keeping things simple.

Sounds like it too complicated so not a large figure and a two family property.

After explaining the below to his lawyer, the lawyer said it was very complicated with several tax implications (which we are trying to avoid of course).

You want an accountant that can help you strategize and who is responsive when you want to know the tax consequences of the decisions you are making throughout the year.House hacking will complicate your tax return.

The 1065 has become increasingly complicated. 

And then you had to go and start over complicating things and pre-selling how losses are ok, no, there not, a loss is a loss and it's no bueno, don't lie to yourself.

Is this a better option in my case, or this too risky/complicated for a newbie?