Real estate investing has started to pique my interest lately, and it seems like it could be a very appealing "career" if you invest wisely. Being a 9-5 slave my whole life isn't appealing to me, which makes real estate investing look even better. Now, I realize when you first start you'll probably need to work at a 9-5 to build a bankroll, and even if you have enough startup money you'll spend a lot of time managing the properties. However, as you continue to buy more (or bigger) properties, eventually you should be able to hire-out management which results in more free time for you. Anyway, I've come up with a very rough plan and was wondering if other investors could share their opinions on it.

First a little background:
I turned 19 at the end of last year, but I'm not currently attending college because I opted to take a year off to "restructure" my life. My father is a higher-up in an interior restoration company. He said I'd be able to get a job in delivery, while doing some after-hours demos on new projects. While delivering, I'd be making decent money while simply driving around the area and dropping off supplies (aka, easy stuff for the money I'd be making). During the demo projects I'd be able to learn more about the repairing aspect which would obviously help when managing properties. For the short-term future (3-4 yrs) I'd be able to live at home. Even though some may consider it lame, it'd be very beneficial long term as I'd be saving a lot on monthly expenses.

Rough plan:
2010: Work full-time while honing my repair skills and reading real estate books/forums.
2011: Join local RE clubs to network, learn about the area, and possibly find properties. Purchase two properties (SFHs or duplexes).
2012: Purchase 3-5 properties depending on financial situation/available deals.
2013: Purchase 3-5 properties
2014: Do a cash-out refinance on a couple of the high-equity properties and use that money to facilitate a bigger purchase if able to(~8 unit, hopefully).

I want to be a buy and hold investor (or buy, fix, rent, refi, & hold). Eventually I hope to sell off the <4 unit properties and plateau at 8-25 unit properties (of course that won't happen for another 7-10 years at minimum). If the 8-25 unit properties are bought wisely, once I have a couple I should be able to take more of a hands-off approach to management and have more free time (and more wealth).

My plan may be a bit aggressive, but with hard work, smart buying, and smart spending I think it'll be possible. So...any thoughts?