Is this the US? Talk to company A about FMLA. FMLA leave can be used intermittently. It wouldn’t necessarily work for court though. If you ask HR about it, they shouldn’t give you a hard time (if they do, that’s just a second case you got lol). Just make sure you have the diagnosis documented.
As for your settlement, I wouldn’t bank on any specific amount. The lawyer might have a better idea but we don’t have anything to compare it to. Also, assuming the attorney is being retained on a contingent fee basis, they will get at least 1/3rd of your settlement. And cases can take years, especially if you end up at trial.