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International - Earned by collecting over 1,000,000 Cuban Pesos
Strategy: Not actually too bad. Once you work through Mafia Wars: Cuba, start buying businesses. Fully upgraded businesses will be able to knock this achievement out in 4 days.
Big Business - Earned by fully upgrading a single Cuban business.
Strategy: Will happen en route to International. Don't worry too much about this or the Tycoon achievement, just buy some businesses and they will pay to upgrade themselves soon enough.
Tycoon - Earned by fully upgrading all Cuban Businesses
Working Man - Earned by doing 20 jobs in one day
Strategy: Easy. They do not have to be different jobs - if you have 20 energy you can just do one energy jobs in the Street Thug tier and earn it easily. Or, you can just work on leveling up and you should get it!
Dependable - Earned by doing a job every day for seven days
Strategy: Do a job once every seven days.
Big Spender - Earned by purchasing an item or service with Reward Points
Strategy: Level up 28 times and buy +4 stat points, or spend your money on some.
Treasure Hunter - Earned by finding a rare item in a mystery crate
Strategy - Buy mystery crates. Sucks because the rares in the mystery crate are pretty poor quality, maybe they will upgrade them at some point
Slum Lord - Earned by owning 30 apartment complexes
Strategy - Buy 30 apartment complexes
Cashing out - Earned by selling 50 Mega Casinoes
Strategy - Buy and sell 50 Mega Casinoes. If you don't have any Mega Casinoes, you can buy and sell them 1 (or 10) at a time to save money.
Getting the Crew Together - Earned by promoting friends to each Top Mafia position
Strategy - Find some friends, promote them to top Mafia.
Crime C.E.O. - Earned by assembling a Top Mafia with all players above level 100
Strategy - Not too bad, by the time you have 50 or so Mafia members, you should be able to find enough to put in your Top Mafia.
Knife Thrower - Earned by looting 10 Butterfly Knives.
Strategy - You should earn this achievement just in the process of leveling up.
Uncle Sam - Earned by owning 50 federal agents.
Strategy - You get federal agents from the "Buy off a Federal Agent" job in the boss tier. They do not have a good drop rate, and the job requires blackmail photos, so I would recommend being a Master Boss before going for this achievement. It might take a few days worth of energy packs to collect enough blackmail photos to get this one.
What's after Trillion? - Earned by depositing 999 Trillion Dollars
Strategy - I'll be surprised if anyone ever gets this legitimately within the year. It took a few weeks for people to hit the 10 trillion mark, so getting 100 times that is going to take quite some time. I think this was just put in the game to give people who have done everything something to do.
Bulletproof - Earned by surviving for over 60 minutes on the Hit List.
Strategy - Surviving on the Hit List takes alot - you need to be able to win a lot of fights on defense (see guide), but you also need to have a lot of health so that you do not get knocked. On the hit list, you can be knocked out even if you win every fight. You can heal every 35 seconds so you need plenty of health at this stage, otherwise you will not last very long on the hitlist. The trick with the hitlist is to have a smaller bounty otherwise everyone will want to get the bigger bounty plus the larger bounties encourage stronger players. If you use the "fight" tab as a refresh button instead of "home" until your energy reaches 100 then quickly move to "health" and restore in good time.
That's Amore - Earned by gifting a Diamond Ring to any player under level 8
Strategy - Get a friend to play, gift them a ring before they get past level 8. In other news, the Diamond Ring crops up on everyone's wishlist!
The Best Offense - Earned by defeating 6 attackers in a row
Strategy - The best way to get attacked 6 times in a row is to get someone to list you on the hitlist after you get an outfitted Mafia of 501. It can be done earlier, but requires a bit of luck. Alternatively, you could have a weaker friend attack you until you get it.