With the 1000 cc motors you would need approx 16 GPM to operate at 60 RPM. You might want to consider a double pump so you have one for each wheel. This ensures that you have power to both wheels and eliminates the need for some type of flow divider.
For steering you have to limit flow to one wheel. This can be done via a good metering directional valve the twould allow you to control both forward and reverse directions.
Yes you will require hydraulic dynamic braking. With hydrostatic drive the drive system is also the braking system. With open loop (gear pumps)This is typically performed with counterbalance valves. These valves are designed to prevent loads from running away.
There are some companies that build planetary drive assemblies that incorporate the motor, counterbalance, gear reduction, and parking brake all in one package. I think PMP is one of these companies but have zero experience with them. I believe that there may also be some options for counterbalance manifold that mounts directly on some wheel motors. Again no experience with these either.
Oil cooling. How long will you be driving this on land. If just short time cooling may not be to much of a concern.
Reservoir sizing: Again lots of factors like drive time, heat generation from pressure losses, etc.
Hopefully this info makes sense and will help you decide on a system.