Having not played the game in probably a year and a half or so, i used to play as Johny, i enjoy the start from nothing or useless and slowly working my way up, but it seems close to impossible to get of the ground now (for me), normal start Johny on normal difficulty, i do lack a lot of game knowledge and haven't read up on all changes made, but the difference is massive compared to my memories.
Difficulty has been increased in some ways, and reduced in other ways. Master's strength, personality and libido can diminish if the current level is not supported by the lifestyle. A master who lacks skills is more dependent on assistant, school or tutors. To get acclimated to how the game works now, it's a good idea to play through the tutorial and read the lectures carefully. We've also updated the in-game help texts that appear when you click on attributes and added a lot of hover tooltips.
With the latest dev build (2.2.2 + minor energy fix and assistant calories adjustment), I started a normal game with M'lord. Immediately rented Taurus apartment, got Isabella, enabled all assistant rules, took the first offered guild contract (D- pet ponygirl). The slave was Pretty, Weakened, Caring, Reactive, Stupid, Cowardly, Open, Slender. She was also slightly spoiled when acquired.
Enabled diet supplements, and enabled rules no masturbation and deny orgasm. Left the rest of her rules at defaults (bedroll, dehydrated food, moderate portion). Bought her athletic leotard, sneakers, cat ears, fluffy paws, leather collar
Day 1: Used encourage and explain her position, tried to have Isabella give her athletics or pet lessons, she refused. Chastised. Sent her to school for pet training, she came back with 4 merit. Rewarded with perfume. End of the day.
Day 2: Encourage and explain her position, sent to school for pet training. 2 merit, rewarded with sweet treat. Racing day, got pony gear for Isabella and took her to the race. She managed to survive the track and finished last (4th). No prize but she advanced from Not a Pony (F-) to Nag (D-).
Day 3: Encourage and explain her position, sent to school for pet training. 1 merit, rewarded with a rooftop stroll. Switched over to athletic leotard and sneakers and did athletics training. Rewarded with sweet treat.
Day 4-6: Encourage, more athletics training. Rewarded with sweet treats. Had slave do gymnastics alone for final 2 points to level up endurance from Weakened to Healthy.
Day 7: Slave is obedient, just needs more common skills for D- rating. Enabled rules behave humility and behave pet. Slave has reached C- pet skill. Master has 2133$ remaining.
During this time, Isabella went to the arena and won her first battle, rewarded with a wedding dress. The master also visited the brothel a couple of times or had sex with Isabella when his libido demanded, and cooked and cleaned for himself a few times to develop his stewardship / relieve Isabella of the task when she was tired after colosseum events.
His personality and strength are fluctuating at the border between B+ and A+ because the standard of living isn't enough to maintain his personality and Isabella is only a B+ cook so the meals are not enough to maintain his strength, but "encourage" and sex are compensating.
Day 8: Isabella gives pony racing lesson, then master gives pony racing lesson. Slave skill reaches D- and she has 5 merit. Spend time together, restaurant. Revealed Hikikomori trait, she doesn't like being out in public. Master has sex with Isabella.
Day 9: Encourage, master gives pony lesson 3x, slave pony skill is C-, 3 merit. Erotic reward, petting. Master has sex with Isabella.
Day 10: End of decade bill was 370 sparks. Isabella's secretary skill leveled up to B+, which will help her reduce the bill for the next decade. One more pony lesson gets slave to B+ pony skill, completing the guild contract requirements. Turning in the contract immediately pays 560 sparks, leaving the master with 2315$ (he started with 2500$).
M'lord's attributes and skills at this point are the same as they were when the game started, but he's given Isabella a 100$ wedding dress, bought her a full set of pony gear, and started her on the path to bringing in supplemental income as both a pony girl and gladiatrix. Considering that the contract slave is Pretty, continuing to train her for a higher rating would be a good option too.
Also note that nothing forces you to immediately rent an apartment. Spending some time in the Slums while developing the master's skills and reputation can be a good strategy if you find it difficult to cover costs of living in an apartment. You can also change the obedience difficulty setting in the in-game options to "easy" (at any time) if you're struggling with training.