Let me start with I'm no expert by any means, I have a lot to learn.
Two weeks after Mooney purchase I took my family to Plum Island 2B2 (2100x50 asphalt, 2300x100 grass), there were no sweaty hands in or out of the paved or grass strip there (I preferred the grass actually).
At home 2400-3000' is the majority of the local airports that I use, most being grass and plenty of trees. I can land the M20F just a few hundred feet longer than a 172, little to no braking being necessary. This is safe and doable, we are not landing on a comet here.
Short fields require nailing your pattern speeds but most of all it's being ahead of the airplane the entire time. When I got my complex check out in the Mooney I asked the instructor for strips 3000' or less so my picture would be familiar when I got it home to 8GA9.
I think that the biggest challenge for a 80+hr pilot will be staying ahead of the airplane in different load and weather conditions. Weight, density altitude, crosswinds, etc. can make a huge difference in landing distance. I would recommend lots of landings at a longer paved strip using the first taxiway off before stepping up to the tree lined 2100' grass strip.