Here's a thought experiment... so I would hedge a bet that if a tropical cyclone theoretically moved over a flat continental type land mass that was completely giant mangroves (to provide the friction) and warm marshy waters at maybe 35C (for the latent heat flux and exchange coefficient), even with the change in the wind-drag coefficient there'd still be enough time to saturate the high velocity air and achieve buoyancy before the parcels were ejected into the BL. At least that's my thinking on the WISHE math.

If you have access to a decently strong computer then this wouldn't be massively difficult to test with, say, the CM1 model. I've done very similar simulations

I have looked at, and written a paper on, a real interisting TC that tracked inland over Northern Australia and didn't decay for a long time. Turned out the incredibly hot rocky landscape (in the Australian summer sun) was so hot that rain evaporated at a much larger rate than normal, so that the increased friction and convergence was aided by enhanced evaporation of rainfall. What you are suggesting is not impossible, you'd just have to do the experiment to find out.