Sure, but he didn't know how long it would take for Sasuke to recover and exactly when he would head out.
Itachi likely possessed lethal information pertaining the Akatsuki and likely possessed the power to physically manifest that lethality of information to reality hence Obito consistently displaying extreme duress regarding matters pertaining Itachi and his associated abilities which makes sense if we instill logicality in the cannonical transpiration of certain key legitimately mind boggling events.
Obito never physically displayed his faciality and characteristic demeanor when faced against Itachi and generally being in his physical presence proximity that's a key notation aspect that implicitly alludes to the readers that he, plentifully feared the mental prospect of approaching and physically scuffling in an extended battlefield simulation VS Itachi, a key aspect of this point being that one couldn't possibly produce a logical counteract debate point against the substantiation that has been extrapolated prior as there exists explicitly 0 legitimate substantiation arguable that exists in the manga that logically penetrates and bypasses the scheme of events that Obito chose to willfully manifest in the grand scheme of things in this manga. Hence I'd say that it's fairly clear that Obito explicitly feared the grandiose prospect of fighting Itachi.
Kyūbi Naruto & CS2 3T Sasuke would've been explicitly extremely lauded entities as it pertains to battle simulations as thier abilities are magnificent enough to physically tackle the likes of Deidara who was physically capable of outspeeding the likes of P2 Team Gai, that comprised of 2 elite speedsters like Lee and Gai, one extremely magnificent CQC Hyuga Secret Arts Style martial artist practitioner like Hyuga Neji, one near 360 degrees omnidirectional spree weapon flicker artist like Ten Ten, and he physically outspeeded and outright outdid mentally all 4 without the slightest glimpse of difficulty without access to both of his arms (one ripped of by Kamui, the other ripped of by KN0 Naruto), and Pain praised him personally in the physical presence of 3 key entities of the organisation (Itachi, Black Zetsu, and Kisame) as being a uniquely exceptional shinobi subsequently after his death at Hebi Sasuke's hands apparently and he (Obito) could've physically infiltrated and snatched a Kid Sasuke well below his prime under Hiruzen's nose who couldn't even physically detect or penetrate the facial superficiality of the Sound 5 Kazekage facade of his intimate student in Orochimaru and the entire whole leaf wouldn't even detect an afterthought of that happening prior to him successfully approaching and placing Kid Sasuke well deep innard his secluded secret hideout. The only reason that can be logically extrapolated on such an atrocious happening not transpiring is likely attributed and intrinsically linked to Itachi's explicit interference on the matter and I believe that much is fairly clear.
Additionally pertaining the question that you've proposed, I think that Itachi's battle instincts have extremely exceptionally advanced to such a quality degree that he can physically anticipate and detect the extremely subtle mental tremor nuances of the opposition with such crystal clear accuracy that he could physically anticipate and vividly imagine Obito's magnificent plans that partly comprised of manipulating an emaciated Nagato on spiritually manifesting a Rinne Tensei lifeforce technique on him to tangentially revitalize and manifest EMS Hashirama Cells assimilated prime Madara Uchiha out of his Uchiha monument coffin and spiritually grabbing Sasuke by mentally convincing and tricking him into believing that approaching and being physically repressed onto the criminal organization was what Itachi truly, and vehemently wanted of like he (Itachi) explicitly strategically orchestrated the Uchiha shrine monument battle into literal obscurity ie., he manifested his plans of applying his secret ideology on the populace, and the alteration of thier minds into believing and making Sasuke out to be a hero and successfully defeating his antagonist criminal brother to the point that his name itself was literally whitewashed as an likely incarnation of evil.