On my first investment property (a duplex) it gave me huge peace of mind to know that I could cash flow at 50% vacancy.

With that life experience I choose to pay early on my mortgage with the goal of having my family's home paid off ASAP, if you can pay cash I recommend it for the peace of mind.P.S.

I like Dave Ramsey, the idea of being debt free and the peace of mind that would come from that but it seems like it would be hard for the average real estate investor to get ahead especially when starting out.

I prefer things as low brain damage and peaceful as possible, life has enough stress. 

Your peace is worth more than being able to invest sooner. 

However, the good side would be that even if it's a burden, I would most likely be able to still save 5K a month, so it would be a good bonus to have while giving me experience about real-estate.If I go with 2, I don't gain experience but I can save in peace, read a lot, and possibly earn more than 5K a month by working over-time.Any kind of insights will be appreciated I really want to gain as much knowledge as much as possible.

For simplicity, they walk away peacefully.

Peace!  

How about calling the police for trespassing and disturbing the peace. 

Be ready with vehicles and bins and a cleanout crew - when the sheriff arrives for physical eviction, they are only there to keep the peace, and usually for only an hour.