He'd better
In colloquial speech, the auxiliary verbs would and had are contracted to ’d, which can be confusing for learners of English and hence explains the OP's perplexity. How do we know whether the ’d in “He'd live in Scotland if he had the choice” is the contracted form of would or had?
In this case, it has to be would i.e. He would live in Scotland if… because of the bare infinitive “live” whereas the auxiliary had is used to construct the Past Perfect tense (had + past participle), e.g. “He had lived in Scotland for the first three years of his life.” Also, we do not use the Past Perfect in the main clause of a conditional sentence, it is only used in the conditional clause, therefore the following is ungrammatical.
He'd lived in Scotland if he had the choice. ❌
The grammatical version would be:
He would have lived [He'd have lived] in Scotland if he had had [he'd had] the choice.
Question tags aka Tag questions
Generally speaking, we use negative tags on positive clauses.
It would be better if he tried harder, wouldn't it?
Contracted form: It'd be better if…, wouldn't it?
He would do better if he tried harder, wouldn't he?
Contracted form: He'd do better if…, wouldn't he?
and positive tags on negative clauses
(i) It can't be better than mine, can it?
(ii) He wouldn't do it, would he?
The expression, had better, which is always followed by the bare infinitive (without to), is an urgent piece of advice given when something ought to/need to/must be done. In informal speech, had is often contracted to 'd or even omitted altogether: “He better try harder next time!” There's usually an implication that if the listener ignores the advice there will be an obvious consequence or negative result.
It had better work, hadn't it?
Contracted form: It'd better work, hadn't it?
He had better try harder, hadn't he?
Contracted form: He'd better…, hadn't he?