I find reading for myself pretty easy, although I've been doing it for a long time now and I started using a cartomancy system which was straight, to the point, and generally not ambiguous. In the system I used, very few of the cards had alternative meanings and a specific court card was selected to represent the querent. It was pretty hard to twist the meanings of playing cards to my fancy, and I think that helped me see the cards, even for myself, with very little bias. My first year or so with tarot I struggled with that, but with practice they began speaking to me almost as bluntly as the playing cards before them.
Sometimes I give readings to my closest friends, and with one of them I can tell her how it is through the cards, even when I don't necessarily like what they're telling me. She prefers being given the harsh truth, though, which makes it easier, and of the few people I regularly read for she is the most receptive and honest. I started doing tarot to get better at seeing other sides, though, and being open to things beyond my perception. Another friend of mine is more difficult to read for, she's much more sensitive and I find myself sugar coating her readings. Reading for my husband is actually the worst, because he's never as "present" as I'd like. He only lets me because I'm his wife
so, I seldom read for him anymore.
Just recently I've begun doing readings for people in the exchange forum here and it's so far ended up being simpler than I expected. I'm thinking about applying for one of those apps or websites, even. At first it was a little stressful, because you don't know these people intimately, but surprisingly that hasn't gotten in the way yet.
With all of my readings, I factor my intuition into the meanings of the cards themselves. Sometimes the intuitive part is pretty quiet or I don't get much of an impression, but often times at least one card screams something at me in a combination of traditional meaning (or a specific meaning, in cases of cards with multiple options) and my intuition. One time the death card was literal. I flipped it over and just knew. It ended up being the truth.