Combat is still too hard except for the easiest of fights.
What I would do is hire an expensive merc like Ayden or Felix, take Bud, Jack or Loren, or maybe the Cultist Monk, give them whipping cane, and just go on a capturing spree. Whipping cane last hit is guaranteed capture on all enemies that can be captured, which means if you encounter a group of four, that's four possible captives. Selling around two to three captives even in quicksell already covers Ayden's, Bud's, Jack's, or Loren's daily upkeep. Cultist Monk is a convict so $0 salary. With a hulking merc like Ayden who has WEGA armor and high enough stats that advance tactics enemies will prioritize him, capturing is made easy and I can go for multiple fights a day, so I may be spending a lot to pay Ayden daily, but he brings me so much more money in return. Note that with Dying World, his ammo pack will be disabled, but that's okay. He just needs to hit bandits with his whipping cane powerstrike. Bud, with enough Affection, will retain his Ammo Pack even at <9 prosperity situations. You will eventually earn enough money and influence, that with a $25,000 loan from the Crystal Heights bank, you can build a workshop. After which, workshop manufacturing will make sure you will not lack for money.
I could also get 30 points in the Divine Juices in Raikan, enough to open the first quest/rumor there which makes Connor available for hire in Warrior's Hall, hire Connor, take his weapon and duraplate armor away, fire Connor, and now I have duraplate armor.
Ayden is already ready for the quartermaster title stats-wise when you get him so make sure he is not an active follower at midnight. He can be Captain of the Guard and Quartermaster.
Do not forget to hire a nurse. Aiko is good starting one. Give her the nurse title and, since she will probably be your solo nurse for a time, do not give her any other job.
Do try the gemstone route. Test it to see if it is viable enough for an early run. I keep saying I will test it but real life keeps getting in the way the whole year. I am a whole lot happier but I also have a whole lot less free time.
I would push back the Dengi Invasion in the game settings page 3 to around 2000 days to be honest. You will not be ready on time.