I absolutely hate when people sing me happy birthday. 

Sometimes a person is so enthralled with what the tool does for them (or thinks it does) or someone they know, that they sing its praises to all who will listen (I'm reminded of the old addage - when all you have is a hamer, everything looks like a nail.)The best course of action is to learn as much as you can; tak to someone you trust; and, choose the course of action that makes the most sense for your circumstances and goals....

If you are considering making "concessions" like tolerating late rent, then you should require that the tenant concedes to sing your lease agreement.

I actually just singed up with amazon Prime, just for the amount of books I'm ordering that are mentioned on the podcast.

We don't have the right to decide when we will and will not enforce parts of the contract.Even if they are month to month the last singed lease is normally still binding, I would do whatever your lease has written that you signed and they signed.Safest course of action if you have to stand in front of a judge.  

I now live in a singe family home with my family as of 2017.

You don't really need their consent to share their info with other agents (they live & breathe networking), and if you do your job well they will be happy to sing your praises to other agents (& guess who just built up a favor in the favor bucket for the next marginal borrower or super fast loan closing needed). 

Would it be smarter to spread it out over 2 properties or put it all into a singe family or maybe a home with a back unit to rent out that we live in?  

Because of having only one gas meter, there is single HVAC hence singe thermostat as well.

Also starting with singe family homes makes it easier to get out if you decide real estate isn't your thing.