MAKING MONEY: EARLY GAME
By "early game" I mean before the Jewel Store Job. By that time, you can have enough money to afford cars and weapons to make your life easier during the main story. All you have to do is ignore some dialogue where Michael and Franklin say they're broke...
MICHAEL (around $2.1 million)
Epsilon missions: $2,000,000 (steal the "apocalypse money" at the end)
Available after "Pulling Favors," Franklin's first tow truck mission. Search for the Epsilon program website on Eyefind and take the test.
Begin these missions as soon as possible. They cost Michael $90k but their eventual $2.1M payout is better than all heists except the last one. To finance them, find hidden packages and rob armored trucks as described below.
You should be able to finish all missions before or around the Jewel Store Heist. When you are required to wear the robes for 10 days, sleep 40 times as M in his bed to advance time, as the game may change his clothes if you switch.
An easy way to steal the money at the end is to break from the convoy right away and take refuge in the semi-covered parking lot at left. Park under the roof to hide from the helicopter and find cover, then take out Epsilon security. Losing the cops is easy too, as there's an LS Customs nearby. Notice that none of the heavy weapons have been unlocked so early in the game, though you can find some hidden around the map.
Hidden packages: $125,000
Available after "Complications." See guide here.
For these you will need a Dinghy, which can be stolen at a number of locations. This is the easiest and quickest way to make money early in the game.
10 armored truck robberies: between $3,000 and $8,000 each
Available after "Complications." See guide here.
These require luck and yield little money, but they're also easy. Keep in mind that random events located outside of Los Santos city limits won't spawn until Trevor is activated, so only a few armored cars are actually available to rob until then.
Alternatives. Michael can also use some of the random events listed below for Trevor.
However, when playing as M you should earn strictly as much money as needed to finance the Epsilon missions, since the Epsilon payout is so high that M will be the richest character no matter what (as he should be, given his backstory).
TREVOR (around $500,000)
Trevor starts with $100,000 and quickly earns an additional $60,000 in "Nervous Ron," so you may want to do some of this as Franklin instead. However, if F starts with $500k (see below), then doing all of these as T is the only way to ensure that he doesn't end up the poorest character for the whole game. Drug shootout (weed farm): around $45,000
Available after "Mr. Phillips" (T only).
See guide here.
Bail bonds: $40,000
Available after "Mr. Phillips" (T only).
$10,000 for each fugitive (or $5,000 if killed).
See guide here.
Deal gone wrong: $25,000
Available after "Mr. Phillips" for T, after "Friends Reunited" for M or F.
See guide here.
Countryside robbery: $10,000
Available after "Mr. Phillips" for T, after "Friends Reunited" for M or F.
See guide here.
Altruist cult: $103,000
Available after "Nervous Ron" (T only), but most hitchhikers are available only after "Friends Reunited."
$1,000 for each hitchhiker, plus four $25,000 briefcases at the camp.
See guide here.
Burial: $60,000 after a few days
Available after "Friends Reunited."
See guide here.
Bike thief: $100,000 in AnimalArk stock
Available after "Friends Reunited."
See guide here.
NB: McKenzie Field isn't worth buying in the early game, since it costs $150,000 and its trafficking missions generate $60,000 at the most.
FRANKLIN (around $500,000)
If you're a returning GTA V player (which I assume is the case since this is 2017), then Franklin starts with $500k and does not need quick money like M or T.
Otherwise, you may do some of the above as F, except for the Epsilon missions, the drug shootout, the altruist cult, and the bail bonds, which aren't available to him. In that case, M will be not only a little richer but a lot richer than either T or F.
MAKING MONEY: MIDDLE GAME
After you've exhausted all money opportunities described above, go through the main story missions. Make sure to unlock Taliana Martinez and Packie McCreary as heist crew members, using their random events. This will help you make more money.
Maximum possible take for Heists (see full guide here)
The Jewel Store Job. Either approach. Michael: $1.2M, Franklin $293k.
The Merryweather Heist. Either approach. Zero.
The Paleto Score. One approach. Michael-Trevor-Franklin: $445k each.
The Bureau Raid. Either approach. Franklin: $240k.
The Big Score. Approach B (obvious). Michael-Trevor-Franklin: $41M each.
More importantly, play the stock market as you progress in the story! Below is a list of missions that are proven to offer a substantial return. In most cases, you will need to either advance the time by sleeping and/or play a couple of missions before the values rise: "Strangers and Freaks" missions work well for this, as they don't advance the story.
The Hotel Assassination. Invest all in Betta stocks before the mission for an immediate 50% return, and in Bilkinton stocks after the mission for a 75-90% return a week later. This should more than double your money.
As is well known, leave the other assassination missions until after the end of the main story, since you'll have a lot more money to invest then.
The Merryweather Heist and the Sonar Collections Dock. After the failed heist on Merryweather, you may purchase the Sonar Collections Dock for $250,000 as any character (all of them will have several times that money at that point). Using the minisub that comes with it, you can collect 30 nuclear waste barrels at the bottom of the ocean. Each pays $23,000, plus a $250,000 award if you collect them all which effectively pays off the property, for a net profit of $640,000.
Buy this property as whichever character needs $640,000 the most at this point. For me it's Trevor, which also fits well story-wise as he operates the minisub in the heist and has one stored at the airfield. Barrels collected by characters who don't own the property will count toward the total of 30, but they will not grant anyone the $23,000 reward.
Minor Turbulence. Buy Vangelico stocks some time before this mission, and no later than right after Patricia's kidnapping. Buy at -30% to -20% and sell at +30% to 40% a few days later.
As M and T are unavailable for a while after Patricia's kidnapping, this mission is actually activated by Franklin (with the green "M" marker). If you haven't invested already by this point, invest with F before activating the mission, and with M & T during the mission itself.
Derailed. Buy Bilkinton stocks before this mission: for some reason, they get a 80% bump after. You need to do a couple of Strangers & Freaks missions for these stocks to rise, as well as advance time to the next Monday.
Bury the Hatchet - Fresh Meat. Gruppe Sechs stocks get a 10-15% bump after "Fresh Meat." However, buy before the earlier mission "Bury the Hatchet," after which you lose control of Michael for a while, so all three characters can benefit.
Legal Trouble - Meltdown. Buy AirEmu stocks before "Legal Trouble" and sell after the mission for around a 15-20% return. When you've cashed in, immediately buy FlyUS stocks, to be sold a few days after "Meltdown" for a 100% return.
Sometimes this doesn't work, so be sure to save pre-investment just in case.
ALSO. The Big Score may become available while you wait for FlyUS stocks. Don't take it before you have finished this investment, as you will need to invest again right after it.
The Third Way. Buy Augury Insurance right before the mission and sell it a few days after for a 100% return. Of course, this only works if you choose option C, which you should anyway...
MAKING MONEY: LATE GAME
Following this strategy, in my latest playthrough I finished the story with $96 million for Michael and about $57 million each for Franklin and Trevor. With that sort of money, it's easy to get to the famed $2.1 billion by the end for all three characters.
Play the other Lester assassination missions, playing the stock market at each turn. There are plenty of guides online that show you how to do so -- below is my strategy.
The Multi-Target Assassination. Buy Debonaire before and sell after for a ~40% return. Buy Redwood after, wait a week, and sell for a whopping ~330% return!
The Vice Assassination. Buy Fruit before and sell after for a ~25% return. Buy Facade after, wait a week, and sell for a ~33% return.
The Bus Assassination. Don't buy anything before. After the mission, buy Vapid, wait a few days (it varies), and sell for a ~100% return.
The Construction Assassination. Buy GoldCoast before and sell after for a ~45% return.
There is no particular time that these have to be done. Personally, I like to spread them out so I can enjoy some Strangers and Freaks in-between.
That being said, the longer you wait, the less money you'll have to invest. This is partly because you don't have any other major money-making opportunities left, and partly because naturally you will want to spend $$$ on weapons, cars, properties, etc.
Hitch lift random event. This can be done anytime, but I usually leave it for last. Buy Tinkle stocks, do the event (see guide here), and sell for a 33% return. This should be enough to put all three characters over the top.
SPENDING MONEY: PROPERTIES
Buying properties according to the characters' backstories is usually a good idea. The game facilitates this by letting only Michael buy movie theaters, for example. Usually, I divide the properties like this:
MICHAEL (spend: $212M, weekly income: $820k)
Cinema Doppler
Tivoli Cinema
Ten Cent Theater
Los Santos Golf Club
Tequi-la-la
FRANKLIN (spend: $1.5M, weekly income: $18k + jobs)
Smoke on the Water
Downtown Cab
LSPD Auto Impound
Los Santos Customs
Hookies
TREVOR (spend: $1.5M, weekly income: $16k + jobs)
McKenzie Field
Vanilla Unicorn
Sonar Collections Dock
Car Scrapyard
Pitchers
The Hen House
As explained before, the Sonar Collections Dock is the most fruitful property. Other jobs associated with properties usually don't pay enough to be worth doing (though some are required to get the weekly income at all).
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