Settlements are negotiated, and are based on the perceived strength of the case, the estimates of the parties as to the probable size of an award of damages should the case go to trial, and perceived PR issues/reputational harms. A second case within a short time might be perceived as a systemic problem which might raise the amount of a damage award, or make punitive damages more likely. On the other hand, it might be regarded as "old news" and reduce the PR pressure for a settlement, and thus the amount offered. Much would depend on the precise circumstances, and any perceived aggravating or mitigating factors. It would also depend on the personal attitude of whoever is doing the negotiating. No one can reasonably predict what might be offered or accepted as a settlement.
In a Federal section 1983 civil rights suit, (42 U.S.C. § 1983) a specifically named officer or officers can be found liable. Indeed, in most cases a specific individual (or individuals) must be named in such suits for the suit to go forward. However, the employer or any relevant union may and often do reimburse an officer for damages awarded in such suits. That depends on local policies and judgements.
See this Nolo page and this page from the Jailhouse Lawyeer's Handbook
42 U.S.C. § 1983 reads:
Every person who, under color of any statute, ordinance, regulation, custom, or usage, of any State or Territory or the District of Columbia, subjects, or causes to be subjected, any citizen of the United States or other person within the jurisdiction thereof to the deprivation of any rights, privileges, or immunities secured by the Constitution and laws, shall be liable to the party injured in an action at law, suit in equity, or other proper proceeding for redress, except that in any action brought against a judicial officer for an act or omission taken in such officer’s judicial capacity, injunctive relief shall not be granted unless a declaratory decree was violated or declaratory relief was unavailable. For the purposes of this section, any Act of Congress applicable exclusively to the District of Columbia shall be considered to be a statute of the District of Columbia.
The words "Every person" at the start impose personal liability. Note that no words in the statute directly impose liability on any governmental organization, such as a police department or city. The liability is strictly personal under sec 1983.