Not so much. The Byzantines did understand how the ghazis operated and the expansionist policy that the was the very foundation of those emirates. Inviting large numbers of turkish cavalry when you didn't have enough forces of your own to check them, is an accident waiting to happen. You don't need 20/20 hindsight to know that Cuman or Italian mercenaries do not constitute the same level of threat as the Anatolian Emirates.
The certainly helps with a smooth transition of power. Have you given any thought how the institutions and administration have evolved over time ?
I think it is plausible that at some point Philanthropenos might try to rebuild the justinian wall that protected the Kassandra Peninsula. After all, Ioannis VII Palaiologos managed to do it as Despot of Thessaloniki.
Moreover, since Philanthropenos moved to seize Imperial Thessaly, I would think plausible that he seized the imperial-held castle of
Anaktoroupolis across Thasos. Between this castle and Thasos, it would be a bit easier to interecept any fleet from Constantinople sailing towards Thessaloniki. Likewise, it is useful for the interception of traffic between Negroponte and the Straits.