I would say that of the songs I sing, I play about 90+ percent of them in the key I am singing, rather than use the transpose button ... this helps me so that if I am just singing while someone else is playing, I remember what key I sing the song in ... Of course there are exceptions, as previously mentioned, if the song is more 'comfortable' to play in a certain key ... one example of this is the beautiful Jobim song "Once I Loved" which I enjoy playing in the 'Real Book' key of Dmin (F), but sing in the key of Amin (C) ... for this song I use the transpose button ...
Any 'instrumentals' that I play are in whatever key they are written in the 'Real Book' or other fake books or music sheets ...
Like chas, I also do not like to play in the key of 'B', and would prefer to play in the key of 'Gb' rather than 'F#' even though they are the same key ... Overall I prefer the 'Flat' keys to the 'Sharp' keys ... as chas said just "a mental thing I guess" ...

One bad feature of using the transpose button - which has happened to me - is, let's say you have a style set up in the KB for a certain song and you have set the style with a -2 transpose setting ... if you are playing with another musician and call out the key as written in the music, and not the transposed key, you are definitely going to have a problem ...

As an add-on to what John C. has said above, when I was studying accordion, there was a fellow who played 'jazz accordion' in the style of the great Art Van Damme ... this guy learned every song in every key ...

no offense intended...& Transposer aside...Id say the "easy way out" is NOT memorizing songs and reading charts as a crutch just my opinion sorry...

Donny ... memorizing is easier for some people than it is for others ... not ALL people have the same talents and capacities ... to many people using charts is a NECESSITY, not a crutch ...
Just another 'side of the coin' ...

Tony dont get me wrong years ago I also relied on charts for shows, But when I went solo I was determined to give the audience my full 150% attention and that said I weaned myself off charts totally and lyrics as a singer/player which in turn makes a better visual stage presence to the audience instead of your eyes always glued to a chart...it can be done and I am proof of it,....just start taking a few songs at a time without reading and after a while you will see that you don't need charts and you can be free to play songs in your own way.....its not that difficult...try the blindfold Technic when playing and also try having people talk to you when you play all the time keep playing without the charts which to me makes you sound more robotic musically....just my personal opinion but what do i know/.....

ciao

You obviously know what is good and works for YOU ... but not everything works for everyone ...
just sayin'

As an example Tony,...I'm sure you can play and sing happy birthday without any charts right?.....
so why not any other song? Just saying....

Of course I can sing a 'riddle' I've sung thousands (?) of times ... and I can perform many of other songs ... but I haven't sung every song I perform thousands of times ...

I ask if ANYONE here can sing and play ANY song they've EVER performed word for word, note for note ... or do we 'ad-lib' a little as long as the melody and meaning of the song is there ...

Repetition is certainly the key.....that's my point....And adlibing ads a creative stamp on a songs overall performance at least memorize the shows set list songs....versus a solo performers head down buried and focused on a sheet I always want to look them right the eyes,...
That said this mother's day dinner is spectacular....yummy...
enjoy tne holiday..

Donny there was no music stand on my jobs for many years. It was difficult for me to memorize; I had to put more time than the average to memorize – but I did it.

With the oncoming of contemporary music I needed for wedding and parties I had to use a music stand. Agreed, I lost something, but I also gained what I needed for the job.

This is going to sound strange. It was me and my guitar and the songs I had memorized. A man backstage asked me for the lyrics to the song, A day in the life of a fool – I could not do it. But when I picked up my guitar I was able to sing the song with ease. The movement going to each chord seemed tied to the lyrics. ???????

You’ll like this one: A song was called – I turned to the page and played the song without any error. Great – but I had turned to the wrong song . aaaaaaaaaaah!

No Donny, you never offend me, it’s all part of the fun we are having, John C.

Several different conversations going on here...

I am a pretty good at transposing. It's something I work on just about every day. I go through the blues, rhythm changes, ii V I, all sorts of licks, scales, Hannon exercises and tunes and play them in all 12 keys.

But yeah, sometimes I still use the transpose function on my keyboard, but I try not to. The chord voicing can sound too high or muddy when using the transpose button. Sometimes I forget to turn it off when going to the next song, now that's embarrassing! And as Tony said, when playing with other musicians, it can be difficult to communicate about the chords and notes of the song when your both playing in different keys.

So I just try to use it in "emergency situations".

When I have time I try to learn the tune in the key it's going to be played in. Every once in awhile, opportunities come up where I'm asked to play on an acoustic piano. Those of course don't have transpose buttons, so I want to ready for those situations and not make excuses like " I can only play on my keyboard" That's silly!

As far as playing from charts vs. memory, I also do a lot of both. Ideally we should have everything memorized. If I have enough advanced notice about a gig, I do put in a lot of prep time trying to memorize or at least being able to play without staring at the page. But there are only so many hours in day to prepare. Sometimes I get last minuet calls to back up singers with no time to prep. I use charts and the transpose function quite a bit in those situations. Anything to get the job done well!