Hello there,
1. One of the series of new endings is buying a property to have some characters to live with the player.
2. Money is not really important in the game, outside of paying the debt, money is not a requirement of any quest/route. Its more a means to an end (better upgrades and QoL)
3. Unlikely to sissify him, he'll stay as a femboy that likes to be handled.
4. There won't be actual beatie in Starmaker. For equine there is Vael (Halloween) and Robert at the farm.