I should have added that there was a first bill of 177 & the 376 came second.

So was the tenant late once and the PM added in the late fee, so even though they are paying on time each month, they never paid the late fee so the PM keeps adding it in and making it worse? 

I figured I could squeeze out an addition $100 monthly per house by adding a bunch of junk fees into the fine print of my leases which my tenants wouldn't pick up on and could take  from their deposits.

We’re also thinking about a STR somewhere.We were able to start here in CA by purchasing a duplex where we live in one half and are now adding onto the property.

I took pre-existing ideas from other members, re-wrote them, and added my own spin to them and posted the draft below.

22% CoC ReturnCash Invested $230K  You made $50,600 in returnBut the sale price is $275KThe math isn't adding up.If you take $275K less that take home profit of $50600.

I would expand my search radius and look for value added properties.

Then you could decide whether that added work is worth that return. 

Converting spaces or adding amenities that will appeal to higher-paying tenants.5.

I would also add 10,000 per month of repair time to go from X to Y. cost of added value is never linear.