I've struggled with this over the years....do I invest in a single machine solution with a newer machine, understanding that I'm going to have 5 digit cash involved? Or is there another option?
For me I've ended up with older, specialized machines....I currently have a 3 machine combination that suits me. I've got a Massey Ferguson 2135 with a loader for dirt/rock work, a Massey 50 for bush hog/finish mowing/tilling/box scraper work, and an International 2504 with a side mount articulated sickle mower for pond bank duty and the occasional high HP towing/pulling needs.
I have the same $$ or more invested in my machines than I would have had I bought a new (or newer) 4X4 machine when it comes down to it. But for me a multiple machine answer has been the best. But I've got plenty of storage and the shop and tools to keep them running. That won't work for everyone.
Dale
"When tempted to fight fire with fire, remember that the Fire Department usually uses water." - anonymous