I myself am going backwards and simplifing my playing style.
(and)
"simple is good"
Agree, but with a caveat. As with everything in the music business, it depends on the crowd, the venue, your own presentation skills, and the musical genre'. A great singer/pianist (ala the late Bobby Short) will probably always be in demand, have a small(er) but super dedicated (and well-heeled) group of followers, and generally play in higher-end venues. Because he is probably (ARGUABLY) better trained than the AVERAGE arranger-playing OMB, he probably has (or could have) a lucrative side business TEACHING (piano/maybe voice) and/or playing for a church/mosque/synagogue.
I have always 'kept it simple' out of necessity due to the limitations of my musical skill set. IN MY OPINION, the secret to being a good arranger player is KNOWING WHAT SOUNDS GOOD. In other words, TASTE. Having some basic arranging skills also helps. After that, having an arranger kb capable of faithfully producing your musical concepts in a LIVE environment without benefit of SMF's or MP3's (else why not just use a synth or WS) is essential. IMO, a TOTL board such as a T4 or PA3x would be the most desirable. If entertaining is more important to you than the quality of the MUSICAL product, then an entry or mid-level arranger such as a KMA or PA500 would work.
So as not to offend the anti-hijack contingent, I won't say more other than to say that this is mostly a lobby for the pianist/singer, guitarist/singer form of musical entertainment which, in my mind, is a more 'organic' way of reaching your audience. Even if you find it more lucrative and/or more attractive to go the arranger/OMB route, you should still try to maintain or develop the skills to pull off this type of gig (I know that some of you already do this). You may be surprised at how rewarding this can be.
chas