The quick answer is, you get Loren and Ansel (and Juno and Michelle) ASAP, that's what you use to make the early battles easy. Even if the latter two seldom hit, they can serve as distractions, or if you prefer the unvarnished truth, meatshields.
Heh, I remember a couple times I tried to cut it too fine (I didn't want to buy a sledge and wanted to use his!) and ended up getting taken down by the guy with the sledgehammer inside the house Juno's leashed to in the beginning. I kept thinking of that scene in "Black Sails" where Jack and Ann had to watch their crew beat to death with a sledgehammer.
The Red Devils are pretty pathetic though, just don't do them first thing. Instead, sell all your food, pelts and merchandise at the Market. Hire Ansel and give him your crossbow and add him as a follower. Hold your nose and put on the skanky leather armor he gives you. Go to Roo's and buy ten tendstims and convo him to start the Headkiller's quest. Go to Walton's and start the 1k guns quest and spend all but 100 on ammo, maybe two clips of 9mm, one more quiver of crossbow bolts and the rest thirty-ought--as much as you can get.
Go to Westside and stop at the clothing store and start the Holiday Dresses quest, stop in and talk to Headkiller's Crew and Threaten them, it's an auto-success. Go down Marston and pick up Loren at Sloppy Moes. Go down to Stokke Hills and save Juno. Now with Loren, Ansel and yourself you can take out the easy ones outside the house, Mad Lewis, the creepy cultist and the punk kid with the 9mm. Maybe one of them will drop and if they do go inside and get those guys. Don't bother with the Vault just yet, even if you do remember the combo. Now go back up Marston and down to Watery Eyes and get the Freebooter's rifle, (upper left) it's the most likely drop on the board, but not guaranteed. There's another idiot in the middle ('Johansson?') you can take out to get money for a massage with Hope Laurel, take it as you're gonna need your stamina. Now go home and pick up the money from Roo's for cowing Headkiller. See what you got in Juno and give her whatever weapon you have and head out again. Kill the idiot on the left, but leave the ones on the lower left alone for now.
Go North this time and start the Kymanto quest and bounties at Town Hall. Go to the Docks and as it should be about 6 go see Sergei, if not quite that time take out the Dockyard Punks, Mr. Hemmel and start the Pai mini-quest. You can use the tunnel or just blow them away if you've had decent luck on drops. At any rate you'll get free guns including a rifle. At this point you should have four attackers, including at minimum two with rifles, make that Loren and Ansel if you start with low Ranged combat. You should have at least one 9mm, probably more. You can finish Kymanto as well as the 1k Guns quest and get Michelle--remember to go back and get the 1200+ from Old Cooney, put Michelle in first position when you go to Westside.
You can now take the Red Devils with ease and do the base Town Hall Bounties and the random one if it's level three or below. Clear the Fort off Marston Avenue as soon as you can, those guys pay out better and that's a big Influence boost. . Remember the guys on Stokke Hills aren't the Ceilor Forest Raiders yet, it's the much easier group and they pay out well too. You should have no problem getting combat armor for your entire team while you upgrade your house each day--note the first day you can improve the house at any time, make it the bedroom and have it be the last thing you do before running out of stamina the first day. I just did it with a pathetic starting character with no charm, melee, Ranged or Manip bonuses and I did it on Grimdark without using any tier bonuses.
Level four and five bounties may have good armor, Coilguns and sometimes Plasma too. It's great when those drop. You can cancel a bounty you don't want at Town Hall, then just come back the next day.
You shouldn't be doing much melee in the very beginning, that's gonna cost you too much in tendstims at that juncture. Have five firing on the line (with rifles as soon as you get them) as quickly as you can.