CAPS deployment in Cirrus
I would deploy CAPS over land if in IMC conditions that exteded below about 1500ft AGL or at night(unless I were visual with a runway or able to get to one within comfortable gliding range). Regarding attempting a landing overland in good VFR I would attempt this if the terrain were good enough ie large enough fields and there was at least some headwind component otherwise I would deploy CAPS, I would try to position myself well 1st ie not over built up area or rocks.
If you are flying a Cirrus regularly, have you joined COPA (Cirrus owners and pilots association)? they run CPPP's (Cirrus pilots proficiency programme) once or twice a year in Europe and they cover matters like this. The last one I went too in Baden Baden last summer included a debrief on most CAPS pulls that have occurred since inception.
Hope you never need to make that decision, happy flying.
Dave Boucher