Fresh GTA 5 always feels broke — you flinch at a box of ammo or a single car upgrade. Use Lester's assassination missions and the stock market right, and all three characters can jump to hundreds of millions overnight.
The Hotel Assassination early in the story is mandatory to progress, so you have to knock it out. Hold the later map hits (Vice, Multi Target, Bus, Construction) until you're ready.
GTA 5 stock payouts come in percent. Start with nothing (say $100,000) and a 50% run only nets $50,000.
Finish the last main-story mission, The Big Score, and Michael, Franklin, and Trevor each walk away with about $25–40 million.
Snowball: start the stock work with $30 million per character, and a 50% bump is $15 million in one hit. Keep rolling that until you hit the in-game cash cap of $2.1 billion.