A lot of guys here buy and work with older saws, because they know what they are doing. Parts are harder to find for some. I prefer current models, even if buying used.If I ignore the price restriction, then what combo of saws and bar length (smaller for pruning, larger for slabbing) would give the best bang-for-the-buck?
If price is not an issue, I would go with a 70cc saw (STIHL 461, Husqvarna 372 or 576, or Makita / Dolmar 7910) for big wood, and a 50cc saw for all around/general use (a variety of STIHL, Husqvarana, Echo, Dolmar/Makita saws to choose from). Some might depend on if there is a good dealer near you for one brand or another that you trust.
Since I trust that price still is an issue, consider an Echo 'Timberwolf' CS-590 as an 'all around' 60cc saw, new with warranty, for $400. Or check local Home Depot rental locations for a used, Makita 6400 (64cc) for $300-$400 (they have other models too). Or a STIHL MS250 (50cc), new for $300.
https://www.homedepot.com/tool-truck-rental/used-tools/mobile/
Add a set of chaps and a forestry helmet for another $100 - $120.
Once you have something to cut with, you can always keep your eye out for something else later, as you see what your first saw can do. Consider a pole saw for branches, rather than climbing into trees, if that is possible.
Philbert