This is where some of the higher Skill Classes and Expert levels can come in handy. If you do start as a Expert Soldier you're pretty much a top-tier merc yourself and can equip two followers with Combat Armor and add Kate and perhaps Doyle and have a well-armored team that can take on most everyone from the outset and doesn't bury you in negative income. Stay away from the nastiest ones like the Black Guardsmen and Gunner on Marsten Avenue until you have Duraplate.
An Expert Slaver, Businessman, Scholar and Doctor can hire Ayden right away, that pretty much ensures the death/capture of your deadliest opponent. That's the other side of the equation, for virtually all combats you can make sure roughly two of their best never get to fire often leaving you nothing more than Pipegun opposition.
Expert Hunter gives you a decent chance to get the drop on the Highwaymen of Darkmere, which is one opponent I wouldn't disturb in an Ironman mode game. Playing my last Enhanced mode start with Ironman the only real time I got white-knuckled was facing them when they had the ambush, they pounded poor Cassius in his Duraplate pretty hard a few times, enough so I didn't seek them out as much as I might have, it was too close a call a few times before I started demurring. Gorun-Iko is another serious problem, I created my character with a 'Godzilla Protocol' so I could play it Ironman and not fear him, but just for fun I saved and tried it the old-school way with Greatswords and prayer--and needed more of the latter. End result was Truls, Cassius and Ayden dead and buried. Then I implemented my 'Godzilla Protocol' and put everyone in Stealth Armor and dared Gorun-Iko to hit me with my 201 starting Dexterity. Yes, I was naughty during character creation, running my age up, maxing Dex on the Attributes screen, then lowering my age to 18 and taking my Skill Classes and Traits.
It did however work, that sonovabitch never touched me or my team. It was the Highwaymen of Darkmere who scared me the most. I did stay away from everyone else until I could ensure they'd never get much of a shot off with a good gun, the Urban Titans still taunt me, I try to ignore them efven though I hate seeing their icon in my city.