Considering Trumps family background I'm not sure he retweets what you've suggested.
He has many faults. But his history has no suggestion of such behaviour.
You are correct, Trump is not an anti-Semite by conviction. He is, however, a cynic who seeks to garner votes and adulation by pandering to the alt-right who are anti-Semites. One brief excerpt from politifact.com:
Trump twice retweeted from the feed of the Twitter account @WhiteGenocideTM, which claims to be located in "Jewmerica" and regularly posts anti-Semitic material, and once from the now-defunct account @cheesedbrit, which had an account page that featured Swastika art and said in part, "we Should have listened to the Austrian chap with the little moustache" -- that is, Adolf Hitler.
Trump and Bannon's courtship, including re-posting their material, of anti-Semite groups helps legitimise/destigmitise these groups. It also brings many viewers to their sites resulting in conversions and advertising revenue. Trump's dog-whistling of racists continued last week with his re-posting of fake news about Muslims which also boosted the visibility of a fringe racist group in UK.
Trump's pandering to anti-Semites (and the accusations of sexual assault) has supposedly caused Ivanka great heartache. What sort of parent would do this when your child, son-in-law, and grandchildren are Jews? A debased cynic. A narcissistic cynic who presumes their daughter's love will prevail no matter what.
I broke my promise not to post again on this topic this year but I have cyber-love and respect for you Saintly so wanted to respond to your fair question.
P.S. Toledo is a beautiful city - love the river around it and the narrow winding streets