I'm still not sure where that leaves my 'intermediate' tasks though - bush hogging around 3 acres and breaking new ground for gardens. I'm concerned those jobs are too big for a fancy mower but too small for a real tractor.
Also on sizing - my local deere dealer (no particular affiliation there, but they are the closest dealer of the big three) recommended an x320 with deck, blower, chains and weights for $7k if I only want to cut the grass and blow the snow, but as I was saying they are pushing for the 1023E (which they have 0% financing on) to do "everything".
I'd agree with Soundguy's approach. Get a basic mower for the lawn work and a compact for the other near-term work like snow removal, bush hogging, food plots, etc. As noted earlier, something a bit larger than the 1023E would give you more capability without costing a great amount more. If you shop among the other good brands, you may or may not find a better value than what you've found so far.
Later you can bring in some big iron for the heavy work, if needed.