Check the contract.

Something has to give: your RE side hustle, your regular job, or your family.

That sounds like a pretty good plan, but I would make a few suggestions:1) if you think it may have had squatters or the previous residents would come back, board up the windows too while you're doing the work. 2) If the property was occupied by the owners or tenants, you may need to file an abandonment notice and wait 10 days or so (check your local laws) before changing the locks. 

When I went online to check them out, they seem to be affiliated with other lenders too.

What are some strategies you recommend to avoid Saturday check-in or check-outs splitting the weekend? 

Since you're into cash flow, you should definitely check out Cleveland OH.

Take a look at AirBNB and VRBO and check the competition to see what's what.Now, personally I don't see this as a great choice.

Check out this blog article:https://www.biggerpockets.com/blog/how-to-invest-in-real-estate-before-turning-21

You might want to check them out to get some thoughts there also.

I wake up and check the app and I go to sleep glued to the app.