LP - first needle drop or 2nd or 3rd??

Been recording my LP’s  to cd for quite a while,
  recently bought the Coven box set (which is simply beautiful, never bought such an amazing box set)
 felt box, flag, heavy pristine LP’s, signed numbered certificate by Jinx, one of the best box sets I’ve ever purchased.

Anyway, question is: would I get the best sound from the first play, or play them all once or twice, to get the proper groove cut, and get the LP’s accustomed to my stylus, and record at the 2nd play?

 P.s. the Coven band predated the first Black Sabbath album by 4 months.
first song is titled Black Sabbath,   Hhhhmmmmmmm.......

first occult album is by Coven, it’s a stellar release, if you haven’t heard of them, worth a listen.
 Parents had 2 Coven records, I remember as a kid, traded them being dumb?
 Box set is simply amazing!!
Handled properly, an LP can endure hundreds and hundreds of playings with no noticeable degradation, so I don't think it matters on which playing you decide to record it. I certainly don't think an LP becomes "accustomed" to a stylus and if it does, it suggests the LP was damaged somehow in playback.

What I do think is critical is that the LP be scrupulously clean. Even a new LP should be cleaned before playing.
An LP can only endure so much depending how the material and how it was recorded.  Gary from Genesis Speakers did a demo and he had special recordings made that could only be played around ten times before he said the sound would degrade.  Go figure.
Better off recording to a high quality cassette tape using an equally high quality cassette deck, preferably a 3 head deck. Some examples would be an Aiwa fd 770 or 990 ( mine) or a nakamichi dragon. This keeps it all analog. Better yet, buy 2 or 3 copies of the albums you like best, will take a lifetime to wear them all out. For example, I believe I own 3-4 copies of Nancy Sinatra country my way, as I play it regularly and happen to love the record. 
I have many LPs I bought in the '60's  Jimmy Witherspoon, Lightnin Hopkins, Beatles, Stones, John Mayall and on and on.
I still play them regularly (played lightnin last night) They are as good as ever. In fact sound better now with set up I can afford in my retired years.
My cart is 1.7 g on the vinyl, barely touching , how can it wear at all?
The type of diamond needle you use does leave traces in the groove of the lp producing noise . Depending on the type they ride on different levels of the groove .

Be it conical , eliptical or line contact . Conical because of its shape and size tend to track the groove on its upper part of the groove . Eliptical goes deeper tracking the groove in a lower level of the groove and because of this tracks information which the conical shape misses .

Line contact because of its shape is capable of tracing very deep in the groove and because of its shape can pickup information on the upper levels of the groove walls . With all three levels noise developes over time . Changing the type of needle used as from conical to eliptical minimizes the noise because you will be tracing a different level . 

Why not go direct to a hard drive?  Then you can dupe to CD, cassette, wax cylinder.....

Just kidding on the last...;)

Why have LPs and listen on CD??

You should copy at the highest resolution available.

Quality of your needle is more important.

You can’t record high resolution on CD, why not just WAV on hard drive in high res instead of 16 bit CD?

Is it for your car stereo ? 

I can understand Vinyl to CD only if you copy somebody else record collection for free :)) 

I do needle drop transfers and find the first run to be quite the one to go with. 
Normally you will also need to set the recording levels so it does not clip. And hence may need a pass over the first side. Unless you know the music from before.
If the record is visibly dirty if bought from the used shop, then I do put it through the ultrasonic cleaners. 
It sure gives convenience for playback. And if you have a top converter and record in 4xDSD, it will be ultra hard to distinguish from the source.
Agree with Cleeds and Slaw. I put all my new LP's through an US cleaning cycle, even new MOFI limited edition boxed sets. And change the record sleeves.

Following expert advice, I brush each record with Tiger Cloth before each play. That stuff really works!
" My cart is 1.7 g on the vinyl, barely touching , how can it wear at all?"

That 1.7 grams is pressing on two tiny contact points in your record groove.   ~50 square micrometers comes to mind.  Then the grooves starts pushing the stylus about.  Plus heat of surface friction.

Think your 100 pound girlfriend walking on 1/4" stiletto heels.  For an instant she puts an equivalent 400 pounds per square inch on the floor.  Now have her balance on one heel and hop around.

It's a wonder to me that a record survives ONE playing.  As my wood flooring has not.  But I still love her.