I am running my numbers and have trouble estimating insurance since I am not sure do I need 3 separate insurance plans(HO6) or 1 to cover all?

It may cover this.

Normally I charge for any special order materials up front, first day of work (demo) I get another chunk to cover labor and materials for the week.

Plan for things to go wrong when you're setting up the deal, that way if they ever do, your *** is covered! 

I buy using a commercial loan for SFH from a local credit union which allows 20% down on purchase and cover 100% of repairs per contractors quote.  

Maybe offer an extra $100/mo to cover their hassle?

He has scholarships and federal unsubsidized loans that cover full tuition, fees and some room and board...but not all.Prob going to need around $20k for college.I have secured a $30k loan using the property for collateral to cover the college expenses.What would you do with the $30k?

I have been looking at a handful of potential deals and the majority of them barely cashflow or are negative if I include myself paying rent (in theory to cover the mortgage).

I own a rental property in Chicago that currently has a lease and the monthly rent covers the mortgage and HOA assessments exactly. 

You need to look at it like the business it is and maximize your profits.You mentioned at the end wanting to, “at least get the tenant to cover half your house payments.”