In addition, my agent screens potential tenants based on my written renting criteria, a huge bonus! 

Bonus questions, what's everyone's opinion on using your own cash to fund as much of the purchase and rehab versus using hard money?

Also a bonus question.

Rent payment on time is a standard requirement in all states.IT would be like giving a employee a bonus for showing up for work on time.

How do I go about budgeting for Contracting as in what's realistic and how do i build a good safety net within that budget without being too generous and without being too conservative?

(bonus points for finding GREAT tenants your first try lol).So we decided to start investing. 

Always invest for cash flow and appreciation is a bonus.

Between a few bonuses at work and then I received a severance package after which I quickly found another, higher paying job - we have close to $300k cash and approximately $5k in "extra" income each month from our salaried jobs after expenses.

Would it be a feasible idea (as long as the numbers work) to co-sign with my brother, using the down payment from our generous grandparents, and to try to get pre-approved by our lender for an FHA loan? 

I am open to someone remote, but it would be a added bonus if i found someone in Chicago.