I need a hard rule we can share with tenants about late payments and evictions.

The best is when they move in and immediately begin making maintenance demands for things they broke themselves, or because some man they lied about not being on the lease is living there and broke it, or one of their endless supply of children broke it  and it's like you still owe like a grand from your deposit maybe don't take such a tone when you fuss over maintenance issues you created in the first place - but God forbid you withhold whatever pithy deposit they did manage to cough up for damages because they go full throttle Jerry Springer guest in 2.2 seconds. 

I'm curious if anyone has created "digital guidebooks" for their STRs? 

Maybe if he pushed a pencil he could have kept working a couple years I don't know.One of the problems with SSDI and other entitlements is that you can't pass rules to deal with every situation.

For instance, with a conservative estimate of 1 month of vacancy per year and 1% of the property value in annual maintenance costs, you could be looking at an additional $2,000+ in costs annually, not to mention the effort and time involved in managing these issues from afar.With all that said, real estate is worth the effort but not all deals are created equal.

And since you are investing to make money and not because you "love" one versus the other, you need to understand the headwinds and opportunities that could create outsized returns for you.  

These 2 points will help me give more pointed suggestions for what you're up against because the tax rules all can be slightly different. 

You can also use a land trust, my attorney has experience with moving properties to an LLC in NC and hasn't had issues but there are ways to be proactive about this and ensure everything is above board and don't create a significant cost. 

I don’t want to run into an issue where I get to many of them and not following rules.* I am only owner financing properties I own outright 

It’s all about creating win-win situations!