Here is my take how such a timeline under the premise of a Judeophilic Hitler might look like......
Jakob Altenberg and Hitler's early adulthood in Vienna and Munich (OTL)
From 1905, Hitler lived a bohemian life in Vienna, financed by orphan's benefits and support from his mother. He worked as a casual labourer and eventually as a painter, selling watercolours of Vienna's sights. The Academy of Fine Arts Vienna rejected him in 1907 and again in 1908, citing "unfitness for painting". The director recommended that Hitler study architecture, which was another of his interests, but he lacked academic credentials as he had not finished secondary school. On 21 December 1907, his mother died of breast cancer. Hitler ran out of money and was forced to live in homeless shelters and men's hostels.
At the time Hitler lived there, Vienna was a hotbed of religious prejudice and racism. Fears of being overrun by immigrants from the East were widespread, and the populist mayor Karl Lueger exploited the rhetoric of virulent anti-Semitism for political effect. German nationalism had a widespread following in the Mariahilf district, where Hitler lived. Hitler read local newspapers such as the Deutsches Volksblatt that fanned prejudice and played on Christian fears of being swamped by an influx of eastern Jews. Hitler also read newspapers that published the main thoughts of philosophers and theoreticians such as Darwin, Nietzsche, Le Bon and Schopenhauer.
So it is not particular odd that when Hitler found was gifted a cheap collection of books on race theory he gladly read them. What is odd, is the man who gave them to Hitler, a certain Jakob Altenberg (1875–1944). He was an Austrian businessman and picture frame dealer. Altenberg, who was Jewish by birth, was a business partner of the young Adolf Hitler in his Vienna period (1909–13). After a discussion of racial theories, Jewish politics etc. Altenberg had the “bright” idea to broaden Hitler’s horizon a bit. Introducing him to Jewish, or Jew friendly figures who had their own ideas about race, war and eugenics.
Ludwig Gumplowicz and Der Rassenkampf (Struggle of the Races)
The first books author Ludwig Gumplowicz (March 9, 1838, Kraków – August 20, 1909, Graz, Austria-Hungary), was one of the founders of European sociology. He was also a jurist and political scientist who taught constitutional and administrative law at the University of Graz and as it happens he was also a Jew.
Gumplowicz became interested in the problem of suppressed ethnic groups very early, being from a Jewish family and coming from Kraków, a city of the former which was first partitioned and later as the Free City of Kraków annexed by Austria-Hungary. He was a lifelong advocate of minorities in the Habsburg Empire, in particular the Slavic speakers. Gumplowicz soon became interested in the later form of sociology of conflict, starting out from the idea of the group (then known as race). He understood race as a social and cultural, rather than a biological phenomenon. He stressed in every way the immeasurably small role of biological heredity and the decisive role of the social environment in the determination of human behavior. While attaching a positive significance to the mixing of races, he noted that pure races had already ceased to exist.
He saw the state as an institution which served various controlling elites at different times. In analysis, he leaned towards macrosociology, predicting that if the minorities of a state became socially integrated, they would break out in war. In his 1909 publication, Der Rassenkampf (Struggle of the Races) he foresaw a world war. During his life he was considered a Social Darwinist, mainly because of his approach to society as an aggregate of groups struggling ruthlessly among themselves for domination.
Nevertheless, he did not deduce his conceptions directly from evolutionary theory and criticized those sociologists (Comte, Spencer, Lilienfeld) who employed biological analogies as an explanatory principle.
Alfred Ploetz and “Die Tüchtigkeit unserer Rasse” (The Viability of Our Race)
The second book in the collection was not written by a Jewish author but nevertheless enlightening to Adolf. Die Tüchtigkeit unserer Rasse (The Viability of Our Race) the German eugenicist Alfred Ploetz (1860-1940). In it he advocated the complete absorption of Jews into the Aryan race: “The Hygiene of the entire human race converges with that of the Aryan race, which apart from a few small races, like the Jewish race – itself quite probably overwhelmingly Aryan in composition – is the cultural race par excellence…. All anti-Semitism is a pointless pursuit – a pursuit whose support will slowly recede with the tide of scientific knowledge and human democracy.”
Ploetz first proposed the theory of racial hygiene (race-based eugenics) in his "Racial Hygiene Basics" (Grundlinien einer Rassenhygiene) in 1895. In 1904 Ploetz founded the periodical "Archiv für Rassen-und Gesellschaftsbiologie" with Fritz Lenz as chief editor, and in 1905 the German Society for Racial Hygiene (Die Berliner Gesellschaft für Rassenhygiene) with 31 members. page [5] In 1907 the society became the "International Society for Racial Hygiene". In 1930 he became an honorary doctor of the University of Munich. Ploetz was a supporter of the Nazi Party, which took power in 1933. Ploetz wrote in April 1933 that he believed Hitler would bring racial hygiene from its previous marginality into the mainstream since the latter had already contacted him long before his meteoric rise, discussion their common ideas on the future of Germany.
In his early writings Ploetz credited Jews as the second highest cultural race after Europeans. He identified no substantial difference in "racial character" between Aryans and Jews, arguing that the mental abilities of Jews and their role in the development of human culture made them indispensable to the "process of racial mix" which would enhance humanity. The high aptitude of the Jews and their outstanding role in the progress of mankind considering men like Jesus, Spinoza (Marx – this name would be edited out of later editions) has to be kindly acknowledged without hesitation...”. A conviction that he carried over into his knew post, distinguishing Germany from other authoritarian regimes of its time.
There were certainly other factors at play but it was probably these books and the cordial relationship Jakob Altenberg that transformed Hitler’s potential anti-sementism into the opposite.
Adolf Hitler, Max Naumann and World War I
In 1914, at the outbreak of World War I, Hitler was living in Munich and voluntarily enlisted in the Bavarian Army. According to a 1924 report by the Bavarian authorities, allowing Hitler to serve was almost certainly an administrative error, since as an Austrian citizen, he should have been returned to Austria. However this little error allowed him to meet, serve and forge a friendship with Max Naumann (12 January 1875 – May 1939). He was the founder of "Verband nationaldeutscher Juden" (League of National German Jews), which called for the elimination of Jewish ethnic identity through Jewish assimilation and served in the Bavarian Army alongside Hitler during World War I (….)
Notes and Sources
All these people are real and from OTL. Max Naumann did serve in the Bavarian Army so he could have met Hitler, but I wanted a stronger theoretical- interllectual framework for Hitlers philo-semitism than a mere friendship. This is just a draft for how a hypothetical timeline might look like.
The Sources are Wikipedia and Jewish Eugenics by John Glad