and if not what would you recommend to get into it sooner?

The agent should be motivated to help since he'd be able to get your house listed sooner. 

Becoming an expert takes time, so choosing a topic sooner than later allows for more study time. 

Since that unemployment income isn't stable, and it's bound to go away sooner rather than later, it's not reliable.

He is month to month, and I let him know I am not going to have him here for September (i.e. 30 days notice, so August would be his last month).I would like to get him to leave sooner if legally possible, for my peace of mind and the safety and comfort of future tenants, if I rent other rooms in the house.  

Probably sooner than later with how this one turned out.

If he wants to invest in RE, I think that could propel him to FIRE sooner but also index funds are great.

Buy sooner.

It could be worse - My PM drinks coffee and reads too long in the mornings, gets on the job by 10, goes to lunch by 1130, the gym by 2 and home by 4. 

Does not matter if its a 15 minute walk with the Dog or Spouse, a hardcore session in the gym, or a nice ride on one of those fancy peletons, get moving in the morning to set the tone for your day!