Having played through the game now and having beaten the second boss on Warden mode, only winding up in the Bar storage room once, I can pretty easily say that its certainly doable, if not a bit grindy to beat the game as it is currently and set yourself up pretty well. Big thing to keep in mind is, pretty much off the bat, to start working on bringing down expenses and bringing up income, it'll help to keep you going in the long run, and as it is currently, with a decent amount of perks that add expenses, as well as the starting title that gives you a bonus of +250 income, I easily wind up earning around 600-800g every day from income alone. Not even counting the bar waitress minigame or the fighting with the guards, and pretty much all enemies (save for those SUPER evasive Goblins, not sure how to improve hitting those that seem to just evade everything you do in the second levels) are a piece of cake to run through once you have slam, cleave, and defensive stance, though having a good bit of perverse/sexual skill, mind stat, and endurance are REALLY good to help keep you in the fights. Honestly, probably the best progression curve I had was just picking up endurance + and mind + first training wise, then doing the other three, and only unlocking mind/endurance 2 before moving onto the second boss. The amount of stamina you'll have is pretty crazy, especially if you get the +300 stam bracelet to boot, and with the energy heal from the mind tree you'll almost NEVER run out of energy in sexual situations, only time I did was due to me pretty much playing it loosy goosy with red fatigue and just barely not being able to scrape by, though with the orgasm passive I got later it likely would have been much easier, and I probably would have even made it through the encounter.
Really, the only thing that this build had issues with, and hardly so at that, was managing to have a low -control, as it was always pretty much -6 /-7, though subjugating a bunch of groups can easily bring you even for the day on that if you play it right, which something that might be good to mention, it seems the enemies that have their backs turned to you in the rooms generally give you less waves than the others, especially less so than those that are guarding doors. Not sure what really determines the number of waves a certain enemy will bring, but I almost exclusively had 1-2, occasionally 3 using this strat in rooms with non moving, wall facing enemies anyways. Helps to get back to bosses a bit easier when needed if a room has someone guarding it.
TLDR to help with early game though, keep income high and expenses low, invest in the personal ones that give a larger income boost initially, and mostly ignore the +10s unless they are really cheap in terms of value, like 100-150 gold. And honestly? Stay in the level 1 zone until you just notice that you stop leveling pretty much. Trying to keep order high to off balance your higher negative control should easily help you to level up, especially with the newbie perk if you choose to use it for the first 7 days, and just milk as many days as you can leveling before you move on to level 2, then mostly progress as normal, grinding a bit before the second boss, and you'll definitely want to take Slam for the slimes at the very least to prevent their regen, and defensive stance to always avoid/block those charged attacks enemies will do at times. Might be a few things I'm missing here and there as far as how my playthrough went, but this carried me all the way through pretty much on Warden mode, and would likely do well in Prisoner mode too, especially if you don't mind winding up with a high slut stat. The real challenge is going to be trying to keep that to a low, or even a 0 and going through the game, and while I can definitely see how it'd be possible after this, its just so much easier to mix combat and lewds to keep things going quick, and well, a bit more enjoyable at the very least for obvious reasons.
Safe to say, definitely excited to see more updates in the future with great content updates like this, personally love the waitress minigame really, even if it could probably use some tweaking to make it a bit more enjoyable or add some spice, as playing it up as a slut pretty much makes it a walk in the park and a gold mine with high stam/mind, especially if you keep drinking off till near the end of your shift to get the big tips and the big lewds. In fact, its probably just safe to say that being a slut is definitely the easy way of playing this game.