How much skin in the game will we need for being first timers.

@Avi Garg we are selling the house for multiple reasons, mainly being to pay off our debt and also move to another nearby city to be closer to family

They have more skin in the game then you do.Make sure you get clear title.

@David Stuart, I'm a California real estate attorney and broker and have dealt with this issue multiple times. 

Do we need to transfer it to an account and then use it for multiple down payments on 3-5 cash flowing properties if we can find them?

There are actually multiple ways to determine depreciable basis. 

How does someone in my position with the experience of finding the best deals, knowing multiple contractors for repairs, and the capacity to put it all together, find private lenders to fund deals?

If you are selling properties within an entity or you are doing multiple properties in 1 year - RMLO is mandatory.

The better location of being closer to downtown would likely reduce vacancies/have way more resell value but then you would need more roommates, does anyone have experience house hacking multiple properties and seeing what worked best? 

If multiple people want to give me money, will they all get a lean on the property or how do you set up the business desk?