First, a second eye on evaluation -- I am an operations manager by trade and I am acutely trained to think of all potential outcomes, costs, risks, etc., and I can lend my expertise at various stages of the deal.

Again, it keeps upfront money in your pocket so it's just a trade-off of down payment vs cashflow you need to analyze.3.

He was the primary property manager and jack of all trades for the properties, but recently he had a massive stroke.

For our first deal I'm willing to take just about anything to learn the trade.

However, given how the market has been, almost everything I'm seeing is trading at retail or above. 

I am a firefighter paramedic by trade and finance and investment is all new to me.

There is that exception that you might find a team that accepts you on a small and I mean very small part but for your $100k trade off, might not be worth it. 

The first hurdle for a 1031 is that it must be for trade or business or investment purposes.

I am thinking of trading it in for a $15K-20K car to put some cash in my pocket to start investing in real estate. 

Depending on the purchase agreement, you may have a provision allowing for delays for up to a certain amount of days without any consequences.