If you still debating on suitable machine, I have both a F-2880 w/60" deck and 3680 w/72" deck on our 4 acre VERY steep property for last 11 years. The property was very overgrown (heavy grass, not woody brush) when we bought it but was able to fully clear with the stock 60" Kubota deck although I did consider a flail. Both these machines had been ex-municipal, so had hard and abusive early years. 2300 hours on that machine not high at all for these units built for heavy commercial/industrial use.
Some mods / Alterations / Notes:
> 3" wheel spacers on main wheels
> Fluid-fill main tires (new turf, but bar better if can find)
> Double rear counter-weight
> Disable seat switch - you do NOT want engine to quit on steep hill!
> Always wear seatbelt - a bike helmet even on steepest terrain
> Wrap-around safety googles & ear protection
> Mower set 4" or higher
> Mow up/down on steepest
> Use Diff-lock on steepest (going up or down)
> 4WD Lock only when going straight as needed
> Lift mower deck for more traction on first pass as needed
> Clean radiator and airfilter often
After living on this coastal Tasmanian property for 12 years, my Kubota F-series are the best machines with local support/parts in my opinion. I had a PowerTrac 1845 for years on a very steep Colorado property with much tree work and snow removal to be done, but no mowing. It was a great machine for that land and circumstances (custom grapple, forks, hyd winch, hyd
chipper, hyd 72" snow blower, fire tank, etc), but never even had a mower for it... considered shipping it downunder, but no regrets.
IMHO, a 63" flail would be fine size-wise if you need the capability for heavy woody brush. Good Luck!!! Cheers, Rip