He took into consideration the fact of having kids while structuring due to legalities of probate (Hopefully a LONG ways away) and my entire financial and business model.

I will certainly take your advice into consideration and I like this route better too. 

From a strictly financial calculation you'll want to invest, but that doesn't take into consideration your emotions and peace of mind.

It really depends on the person's track record, and I take other factors into consideration, like credit score, Landlord reference, etc.

The other consideration is whether you can buy bigger with the same cash but higher leverage (instead of spending so much on repairs, get something more stabilized and apply all the cash for down).

I can agree with all the people who say hardwood is the best choice for A class homes, especially flipping, but for rentals if LVP is a consideration, Peel-and-Stick should be taken seriously. 

If I rent for $1,800, I'm pocketing $264.84 each month but i'm not taking into consideration vacancy cost, capex, repairs + maint.

He said two considerations you'll want to make here are using Internal Rate of Return and Return on Equity.

If the tree caused considerable damage to your property, I'd look at getting insurance involved. 

Based on the impression I got from your posting, the tenant's bike storage is a considerable inconvenience to you.