I mean, besides the player-compensation issue, that is the other massive hurdle—and one that I think is ultimately more substantial to actual playing the season (as opposed to just setting a date for starting it).
If a player tests positive, there's a non-trivial chance it'll end up being more than one player by the time they've ascertained there's a positive case—so what happens if a sixth of the proposed thirty-man active roster is suddenly medically ineligible? Or if two teams playing a three-game series suddenly each lose half their players to medical ineligibility? And, even if cases are caught at the single-player level, how many individual cases can a roster withstand? What if a player tests negative, but a household member comes up positive? Is that player medically ineligible anyways, as a precaution?
Lots of questions—and of course none of this even mentions how competitively fraught everything could get. For instance, say the Braves were to lose Acuña, Albies, and Swanson for a 14–21-day stretch in precautionary quarantine, and that happens to coincide with a few series against top division rivals. Or say the Twins lose their whole bullpen for 14–21 days right before the postseason?
Going to be strange baseball, if there's a season at all, for a hell of a host of reasons.