What we find is that owners in your position can do well in a set of ideal circumstances:  the home is in great condition, they find excellent tenants who treat the property with care, and nothing crazy happens. 

Depending on the facts and circumstances of the agreement, it could either be treated either1) the sale occurs as of the original agreement date, and then your taxable gain is generally spread out over the life of the principal payments as an installment sale (although I should mention any depreciation you've taken on your property could affect this), or2) the sale does not occur until the lease option is exercised, and gain reported at that time.

Will absolutely push the due diligence time in order to make the decision and if the seller is unwilling given the circumstances, i think as you implied that is perhaps a bigger red flag than anything!

We reluctantly signed a 2nd year with him because we did get all of his late payments and the property was taken care of.During the 2nd year, I let one late payment slide as a courtesy due to tenant family circumstances.

Unfortunately, due to an unforeseen event, me and my friend are no longer able to attend, but our loss could be your gain!

At the end of the day, everyone's circumstance is unique so it is best to speak with a professional.

Would I need a broker's license to manage this property under these circumstances?

I don't appreciate these giant real estate personalities or influencers/motivators because it's stupid and unethical for people with kids and families of limited circumstances to be told they have a good probability of owning a "thousand doors." 

Another thing to keep in mind is that a structure is usually specific to an individuals own set of facts and circumstances. 

The IRS would look at the facts and circumstances.