(sometimes the caps bend or break trying to get them off) All in all, it's not a complicated job for a Roofer that knows tile roofs.

DST's are complicated.  

Don’t make it complicated.

These deals are risky and complicated.

The one and only time I've heard Dave Ramsey address the idea of "good debt" and "bad debt" with enough time given to make a complicated point, he talked about how difficult it is, specifically in real estate, to precisely calculate the risk of these investments. 

The feedback I usually get is that buyers wanted to assume the loan but the process was lengthy and complicated, and buyers eventually moved on leaving the seller with no equity and option to sell other than writing a fat check at the closing table since they had to continue to lower their price.

If the plans are super detailed or complicated forget about it. 

You are making it more complicated than it needs to be.

@David G. your making this WAY more complicated than it need be. 

Something tells me you won't be working 4,060 hours to do so - 80 hours a week year round.If it is a more active rental model that it is not considered "rental" income, then you would need to put in at least 100 hours with that being more than anyone else (employees, contractors, management company, etc), or you would need to put in at least 500 hours.So your "quick" question is actually fairly complicated.