Long story short... you will likely need a liquidity event for your shares to be sold for cash.
This could be though an acquisition, IPO, or the board deciding to let you sell your shares (usually back to the company via the right of first refusal).
Your shares are sort of "worthless" until one of these events, that is the risk you take by allowing some of your compensation to be delivered in private stock.
The good news is they are offering you a .25% vested stake and a shorter-than-normal vesting period of 3 years. Once those shares vest they are yours forever, or until you sell. If you decide to leave the company there is a chance they will offer to buy you out of your vested shares, that is where you can make some cash.
"However, the bigger news is that Microsoft plans to integrate the functionality from its mobile calendaring app Sunrise into Outlook, then shutter the Sunrise application when the integration completes."
* I am assuming you are applying/interviewing for developer jobs.
Stop worrying about being "too bubbly or enthusiastic", coming across young & organizing meetups.
Start worrying about not having outside work projects & being weak on technical questions.
You need to be able to prove to a potential employer that you can do the job. Organizing meetups is nice but does not show anything about your development skills. A github profile with a few projects related to the type of development you want to get into will do much more for you than anything else.
To me, it does not require any more or less skill to produce compared to other design trends (Web 2.0, Skeuomorphism, ect). Flat design not new and it is not a cop-out.
Your take-home pay should be somewhere in the $2500/mo range. That leaves you with about $600,after paying your rent and parents mortgage, for everything else in life (utilities, cellphone, ect). That's not likely enough to save up for the things you mention.
Food: As cheap or expensive as you want. Typical lunch in the city will run $10-$15. Buy cheap groceries and bring a lunch every day.
Commute: Depends on where in NJ you are. Hopefully you are close to PATH, if not you will likely take a NJ Transit train/bus.
Reference: I am an iOS Engineer, working in Manhattan, living in Brooklyn. Have been here 5.5 yrs.
Pretty straight forward here... take the cash. With a wife and family, you need some savings for a rainy day. I don't know your specific situation, but I rarely count on options as money in the bank.
It depends on how polished you are looking to get and how much experience you have with Photoshop/Illustrator and general front-end development.
If you are simply looking to get some iOS experience, you should be able to hack together the UX/UI yourself. If you are trying to launch a business, design will be imperative for success. Show me 1 poorly designed, truly successful App in the App Store.
Like everyone says now-a-days... I'd suggest focusing on the MVP concept and build just the core features, with excellent design and UX.
I can not recommend these more. Super comfortable, closed back, huge drivers, great balanced sound, affordable. The "winged" support makes these babies wear-able all day and night.
I like the concept, and am waiting for someone to execute on it well.
As for your FaceToFriend site... It is very difficult to figure out exactly what to do after logging in. You need to direct the user (especially a new user) to the key feature/areas. If the "I Want To Talk About..." search box is where you go to get rolling, you have lost already.
This could be though an acquisition, IPO, or the board deciding to let you sell your shares (usually back to the company via the right of first refusal).
Your shares are sort of "worthless" until one of these events, that is the risk you take by allowing some of your compensation to be delivered in private stock.
The good news is they are offering you a .25% vested stake and a shorter-than-normal vesting period of 3 years. Once those shares vest they are yours forever, or until you sell. If you decide to leave the company there is a chance they will offer to buy you out of your vested shares, that is where you can make some cash.