Where the 808 actually came from
The Roland TR-808 shipped in 1980, sold badly and was discontinued in 1983. Its bass drum voice was an analogue circuit - a bridged-T oscillator whose long, tuned decay was, by the standards of the time, a flaw: it sounded nothing like a real kick drum. Hip-hop and electro producers bought the machines second-hand precisely because of that flaw, and forty years later the "808" no longer refers to a drum machine at all. It refers to that sound: a low sine with a pitch drop and a long tail, used as bass.
Sample or synthesise?
Both are legitimate and they fail differently. A sample gives you a finished character instantly, but pitching it far from its original note stretches it - go down a fifth and the decay lengthens and the transient smears. A synthesised 808 is always in tune at any pitch because it is generated, and every part of it stays adjustable while you arrange. For a bassline that moves through a progression, synthesis wins on consistency.
The kick problem, honestly
The most common 808 complaint is not about the 808. It is that the kick and the 808 occupy the same frequencies at the same instant, and the two waveforms partially cancel - which is heard as a low end that has energy but no impact. Three fixes, in order of how much they cost you: do not place them on the same step; sidechain the 808 to duck under the kick; or high-pass the kick and let the 808 own everything below 80 Hz. The first is free and works better than people expect. The beat making hub covers where each one lands in the bar.