I'd just play as a caravan owner (lol brain can't form words). If you are using mods... well talk about experience enhancers...
This is how I play or start out most of my NV games:
-Start out with the Doc Mitchell thing but add a role playing twist to it, such as; Chose to answer the questions he asks based off of what you actually see or feel, hell nod a few times.
-Try to match your appearance as yourself, not necessary but it helps none the less. Don't make that good looking guy or that hot girl.
-Don't choose overpowering skills or traits. I.E. Energy Weapons or even guns(Unless you are experienced with guns in real life) lockpick, maybe speech even.
-SPECIAL: Unless you are a jock-jaw snapping- can bench 365 pounds- body builder(highly doubt if you are playing video games and have enough time to do this, haha JK) keep strength low like 5 or below, since 5 seems pretty balanced for most SPECIAL skills. Perception, tough one, keep low, you don;t want a "magical eye" compass do you(Don't say yes, if you do stop here)(Don't actually stop here though)? Endurance, I'd keep low, 4 or below, because it makes the game more challenging. Charisma, again depends on your personal appearance, hopefully you follow the above appearance note. I'd keep it at five because it is balanced, people won't have a high or low opinion about you. Intelligence, another tough one to explain. Look at your age, younger such as 13 and above should keep it low, since, well, your still in school, at least you should be. your knowledge isn't as "advanced" as some older people(I will not explain this in full since that will take forever). If you are older I'd say keep your intelligence medium to high. NEVER 10, unless you are really smart in real life, don't lie to yourself. No one is so smart that they can move things with their minds (Shut it if you say you can). Agility, depends on you again, flexible gymnast: Shoot for a high agility (NOT 10). If you are not so athletic(Don't mean to offend anyone) keep your agility to 5 or below. Luck, will be explained later.
-ALL YOUR SPECIAL STATS WILL DIFFER BASED ON YOU IN REAL LIFE(it's called role playing for a reason people) YOU CAN'T FOLLOW THIS GUIDE EXACTLY SINCE AGILITY, INTELLIGENCE, STRENGTH, ECT WILL DIFFER. Make sense?
-hardcoe mod is always nice but I wouldn't worry about using it since it really isn't balanced imo.
-Set difficulty to hard or very hard, or if you have a realism mod, use it, like Arwens for example.
-Find a nice brahmin companion mod. After this I suggest hording items, anything you find really(Think about if the world did "end", what items would you find useful.
-A camp fire mod would be nice, but only make one if you have the "appropriate tools to actually do it" i.e. sticks or a throwing spear, you know what I mean.
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Spoiler If you get Benny's lighter, I like to think of that as a "unlimited fire source"
-Travel the roads, or if you are daring go off road to explore.
-Don't use powerful weapons. Play as a wastelander, poor- well off as I see it. Trade when ever possible, especially if you meet an npc on the road.
-NO FAST TRAVEL. This is an immersion breaking thing in my opinion. Wait is ok every once in a while but I would stay away from it as much as possible. Why? Immersion breaking and who would wait for an hour or up, standing in the same place?
-Try to stay at abandoned buildings or hotels every night.
-Make night dangerous... in your mind and game, really good role playing especially near Death Claw territory.
-IF you do decide to buy a powerful weapon, buy it from Gun Runners. Why? Most expensive, hell unless you find it in the wastes, hopefully not so early, why would some one sell you one for like 500 caps? Doesn't make sense, buy it from Gun Runners. They are trusting. good condition, and are priced fairly well.
-Don't be a gamble master. No one is 'invincible" when it comes to gambling, and it is called luck for a reason, so try making your luck skill 5 or below!
-Try focusing your wealth on the trade not the game.
-Along with wealth, feel free to buy necessities that you can't find out in the wastes too much, i.e. clothes, food, pure water, ect.
-Don't be afraid to spend, spend, spend! It's all about the RP here. You can't expect to survive with no food, ammo(Providing you even use a gun) and the same clothes for ever right?
-Stay away from
joining major factions. Didn't say you can't trade with them, just don't try to get involved(Will explain this in full later down the road) with them. Reason being, they ask you to do "heroic" tasks. It is highly unlikely that a simple, poor, trader will rise to lead an army to victory and control the wastes with an iron fist...(Shut it).
-Along with factions, try to play the neutral guy(or gal) here. You want as much trading and business as this dead world can give. Granted you can help citizens and wastelanders if you wish but if it is dangerous in real life, don't do it in the game. i.e. Faction officer: "Save my men from the legion!" You: "Hehe ok..." Don't do stuff like that. Companion quests are always good and can give you the short break you need from the simple life.
-Companions: Great to have. I mean, who doesn't want a friend out there, right? Of course I'm right. Since they really can't hurt your status with major factions, it is all good.
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FOR EXTREME PLAYERS ONLY: If you die, its over, gone, buried, "Knock knock... who's there? Death..." This is role playing to the max. In real life, you don't get second chances: BOOM! Head flies off. You won't have the chance to say: "Hehe, I'll just reload a save." Why should you do it in a game that you are role playing in?
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EXTREME (and non-extreme)
CONTINUED: Along with second chances... once you pass/ or fail a speech check, get locked out of a terminal, break a lock, its over. Done, zero, no reloading to try again.
This is also applied to non-extreme players!!! -Don't use a "perk every level" mod. Makes the game more challenging.
-When it comes to leveling, don't blast all you points into your favorite skill(You energy weapon crazies you!). Only put them into the skills you have used so far. If you used repair alot, put some into repair and so on.
-Refrain from heavy combat, especially you extreme players. It makes no sense for you to charge into a NCR-Legion battle. One: it breaks the no joining factions statement, and two would you do that in real life?
<--- Ask this alot of times when making decisions in game.All I can think of, I'll add more if I come up with something else.
Enjoy! Hope you have as much fun as I did/still do.
OH! PM me if you want a list of mods to enhance your playing with this (PC only).