I like to have the city ready for an immediate advance several levels up, before I start to distribute pottery, and to distribute wine only at the moment, when it becomes really necessary. I also always try to bring all housing to the current top level : Small Casa, then Medium Insulae, then - if needed - to Large or Grand Insulae. With such approach it is possible to win all assignments without even starting to distribute wine (i.e. without villas) - except for Londinium and Massilia. This file can show you, that it is possible to win all career scenarios without building a single Palace. After unzipping the downloaded file you will find 3 saves showing the most important moments - start of pottery distribution, start of wine distribution, prosperity 85.
Mass_1.sav - January 112 - stabilized population of nearly 6000 citizens, all residing in Small Casa (a few Large tents can be found in production areas). No pottery distributed or exported until this moment, 90 in warehouses - that was the right moment to start distribution and export. City has reached nearly the full size, only a few houses (one new small block, and some houses in existing ones to increase the density) will be built until the end of this assignment. Infrastructure is ready for instant jump to Medium Insulae - enough furniture on stock, all services already available. As soon as profits from pottery export will come, I will restrict oil export to advance to Large and Grand Insulae.
Mass_2.sav - May 119 - well over 60% residing in Grand Insulae, 25% in Large Insulae. Only few houses are not at Insulae level. Prosperity 68, not rising because of housing quality. You could get around 75 when all housing under Medium Insulae (and maybe part of MI as well) is demolished at the end of the year - but that's not enough. Time to begin with wine distribution - very cautiously, otherwise there will be too many Villas. It is necessary to manipulate with Stockpiling, so that always only a part of markets gets the wine. Number of tents is already minimized. Great part of industry will be switched off soon to compensate the loss of workforce due to villas. No problem, as there is enough goods on stock. Prosperity needs final boost.
Mass_3.sav - January 121 - prosperity 85, requirement met. Population is too small now, remains building of some housing blocks and the rest will come as villas devolve to Insulae again (no more wine). Large Villa is the top housing level, I never started to distribute third type of food.