I lived well below my means, worked a full time job for years while doing this on the side, persisted when others did not... and now I am enjoying the fruits of my labor.  

You'll need to really look at yourself and understand what you do well and enjoy, at the end of the day if you enjoy what you do you'll have more drive be successful everyday. 

Even if straight off a cliff. 

I've been following the build-to-rent method for some time and even lived in one for 2 years.

I feel like a Daisy-Chain would muck up my Timeline or even the whole Deal.As long as everything is in writing and I get my Fee, does it matter?

I agree get your hands dirty, you will learn, tenants can wait for weekends or evenings for most issues if you DIY.Good Luck!  

I hope I added a little more clarity, I know that even in this post I am going back and forth.Thank you.

Even a clock is right twice a day. 

If not, I most definitely would reach out to the tenant, introduce myself and ask if they are going to be out by the 31st or the 1st, I would communicate  to the tenant as if I know they were told they are expected to leave, otherwise you may find they "do not know" they need to leave even if they actually know they need to leave....In the case they claim they are not aware they need to leave, you would need to follow the laws in the state you purchased the property, usually you can find that info on the states judicial branch or speak with a landlord tenant attorney. 

Even if it's just a small, local deal, I’m curious!