I am probably similar to you where I never want to retire but want to have the comfort to know if I fail pursuing a dream that it doesn't harm my children.

Your classic newbie move is to focus on one deal for three months and then when it fails, the pipeline is a clean as a newly dug PVC sewer line.

I have seen several fail due to lawsuits and insufficent coverage. 

A couple of questions to ask... do they lock you in for a year or can you terminate the agreement with not penalty if they fail to perform? 

Therefore, that fee is there to make sure that they are getting the job done the first time.Anyone who is saying that they can do a great PM job and won't charge you anything besides the monthly fee, is most likely going to fail out of the business because they won't make enough to stay in business, hire and grow.It is very important to understand all the fees associated with a PM, but I encourage you and your friend to not shy away from a company right away if you see they have fees on other things other than a monthly cut.

STRs are saturated here and failed STRs are starting to saturate the MTR space. 

Nothing fails like success.3.

I ended up owning about 250 of these.. and having to sell them off taking loss's virtually everyone of them it was a blood bath for us HML in 08 to 2010.. and not anything I want to ever repeat.. those that started lending HM post 2011 have had the rising tide great market situation but even with the good market people fail all the time for various reasons. 

Didn't they already fail the criminal background check just by being an illegal immigrant?

Your muscles will be sore every day, you will see people doing much better than you, and you will constantly fail.