If you are buying your first setup: start with a brief-style harness. Fewer straps to get wrong, and it stays put without much adjustment.
If you already own a harness: measure the O-ring before buying anything else. Base diameter, not length. This is the single most common ordering mistake in the category.
If pegging is new to either of you: the first-timer's guide is worth ten minutes. Size and angle are where it goes wrong, and neither is fixed by a better harness.
If the wearer wants to feel something too: strapless or a vibrating harness. A standard harness transmits very little, which surprises people who expected otherwise.
On lube: more than you think, and reapply. Neither person can feel what the toy is doing, which is exactly why this needs more than partnered sex does. Lubricants has the toy-safe ones.