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Go to Asculum.  Sleep in the bedroom until the day calendar in the corner says "Dies Veneris" - that's the day he's in the town square.

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Got to meet him. He said come back next week. Did that. He said come back the next week... again. Grinding, because he's not there the next time. I'll try another week.

That might be a quest error.  Try it a couple more times, please.  Hundreds of people have played that quest though

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I started over, and got past it. Probably need to start over again, since I'm out of money. :)

Only buy Fasti and Inka to start.  Train them and set them to whoring.  The bordello is a shit hole, so no clients will be happy, but you can still make some money.  When you are in real need of cash, train your rhetoric in the basilica and start taking clients.  A good case can get you 4000 sestertii

Good advice. Working with Fasti only at the moment. 

Is it wiser to set the supply purchases manually, or let the madam do it? Minimums seems to be extreme, if automatically purchased.

Alfidia is *terrible* at managing the bordello until you get her trained up.  Buy your own goods in the beginning if you can stay on top of it.

I need one last piece of advice, really. The balance between patience and discipline is hard to find. Ignore their reluctance, and they get worse. Beat them too much, and they get worse. I've tried mixing up the sexual and non-sexual requests, but that also seems random.

What is the best way to raise their acceptance? In one playthrough, I've had all three girls fully trained in all aspects, yet their other stats never rise. Doesn't affection for the MC ever develop?

Each girl will have three loyalty quests, more or less.  Their willingness to be obedient increases with the first, and affection begins with the second.  It sounds like you're mostly at the end of the existing content.  Moree to come soonish.