The trunk form factor is excellent for fitting in taxis - even LNG models with the tank in the trunk configuration I've carried a trunk for the past 4 years across NA and SEA without any issues I tend to use the lid to store clothing, especially stull that needs to avoid wrinkles and us the bottom to store everything else
As for public transit, a trunk will likely make life generally easier as you probably won't need any additional travel bags So you can just throw your laptop case on top and only manage "one" bag. Moreover in hot sweaty climes you'll work and sweat less. The rare times this configuration is more work is very brief, like when lifting over tall curbs or small steps, and not terribly common. I frequently walk over a mile with my trunk to and from transit without issue.
Of course for this to work best, wheel quality is among the biggest concerns So choosing a brand with robust and long lasting wheels is an absolute must and likely worth the premium for it