I find I definitely get more satisfaction from my Grimdark run with no re-loading. It also means time passes faster so I get farther into it quicker. It's probably a wise move to steer away from the Tier-6s for now, it also seems Grimdark changed the odds of getting one as they're no longer the most likely bounty like they were for a while, seemingly two out of every three or so.
Give Bud that plasma gun and keep him happy by frequent 'carousing' sessions at Dockgrave. Poker is probably too rich for your blood (and skill) at that juncture but the carousing bonuses really add up with time. I ended up getting a 40 performance, the only universe in which I can sing on tune!
I just ignore Bud's attention whore trait and let him get pissed. I do train him though. He's still got a ways to go but he's currently sitting at 80 aim and using a plasma gun even though he misses a fair amount of time with it still. I may do some poker after I take the classes that give gambling bonuses but I haven't started on that yet.
For the tier 5 bounties I give one to Doyle as well and use one on my main. At some point Grim changed it so that you actually get a small amount of ammo with a gun drop so I've actually never had to buy any plasma ammo. I just randomly find a bit here and there. So if I only use them on the hard fights I'm not really missing the free ammo of the top tiers. Too bad Dexter won't give up that pistol but he's pretty good with it, and Aiko is closing in on high enough aim to be able to use a plasma in a pinch as well.
I do find that money is WAY more scarce now though. It's about day 30 now and I've only bought basic upgrades for my house (maxed out bedroom and garden, 1 upgrade in all the other rooms, plus gazebo and a level 3 shrine. I've also only bought the aim implant, the healing implant, and duraplate for myself and only 1 suit of duraplate for my mercs (Doyle is still my tank). In addition to the fact that I'm doing more tier 1-4 bounties than I am tier 5 so far, it's pretty common for combat to have zero weapon drops. I've had decent luck on the tier 5s so far though and have gotten 3 plasma guns so far.
In addition to the combat, the no F5 thing also means I decided to wait longer to seduce any of the girls. So instead I'm training up stamina on Mae, the valkrie, and Rebecca and those are currently my only girls. I have Mae and Rebecca at 80 now and the valkrie is up next so Rebecca is going to head back to the arena again for a bit, but without F5 Rebecca can only reliably do the $50 ordinary opponents with a weapon reliably. She can't beat anyone with fists. So I don't plan on having her do the arena very long. Trying to scrounge up enough money to buy Aria now so I can alternate between the valkrie and Aria in there while I train them up to be combat monsters. The valkrie can beat the heroic opponents with a sledgehammer 100% of the time but not the legendary. I haven't found a way to use the power katana in the arena. Do you have to give the girl a power katana before you send her to the arena for that to work? I do have a couple.
I can't do the stokke hills or marston ave bosses yet since they randomly hit anyone and me and Doyle are the only ones with armor so far. I also took the crafting perk this time since grinding out crafting increases annoys me. The crafting perk starts me off with enough that I can at least make swords/crossbows/pistols that actually count towards faction donations instead of dozens of daggers.
I'm definitely going to want to spend some quality time training melee with the valkrie soon, both for her arena benefit and also for my ability to capture slaves. Since I didn't start with melee master this time I'm capturing a LOT less slaves. It's pretty common for me to miss with that cane so unless it's an important capture like the valkrie I only try once or twice before just giving up and shooting them.