I usually consider the "Use frequency-to-cost" ratio.
Items I use frequently or which are ceap, I buy. Like DMMs, LCR meter, lab power suppy, signal generator, scope and the infamous transistor tester, battery chargers.
Items I need but use infrequently, I buy second hand or repair. Like Psophometer, wideband AC milivoltmenter.
Otherwise very expensive or not readily available items, I build. Like audio analyser (soundcard + input and output amplifiers), transistor curve tracer, opto isolation amplifier, voltage regulator tester, opamp tester.