Perspectives on Strategy moving forward

[Andrew Caleb Bell]

Looking for concrete info concerning this "hypothetical" situation and/or some strategies/options moving forward.

Scenario: Bill owns 3 rentals. 
Rental 1 is paid for and is 1 door of a duplex. Est Worth 90-100k Rent @ 1050
Rental 2 is a 3/2 that has a mortgage of 105,000 with a remaining 80k. Est Worth 145-165k. Rents @ 1250
Rental 3 is owned with family member and is paid for. Current value around 65-75k.  Attempting to get rents to 700.

Bill is partnering with his brother and established a series LLC in which to get transition properties into. Bills brother John has around 200k cash on hand to contribute to the startup.

Bill has been in the rental game for 10 years, but because of work has been very passive.  He is unaware of all the various options and opportunities.  Especially when it comes to financing.  Because of Bills and Johns mother who is sick, they would like to have as much positive cash flow in the next 5-7 years to offset care costs.  They understand this will limit some growth potential, but at this point its best.  

What should Bill and John be looking to do?