Finally getting my feet wet in Gainesville, Florida

Well, as my title says I am finally getting into real estate after watching from the outside for a long long time. I am 28 y/o and have family in real estate, though none are investors. Most are in title ins. I've wanted to be my own boss and generate income through real estate for a long time now. I've read some books here and there (probably the wrong ones) and never had the capital or the guts to jump in. I am currently in school for Nursing and I tell people all the time that this is just to fund my real estate future. I now have the capital to purchase my first property. My tentative plan forward is to purchase a sfh and I will live in it for the next four years or so while I finish up school (grad. in sept '14) and I will rent the spare bedrooms to help cover the mortgage then when I move (or maybe sooner) I will buy my next property and so on. I will keep the first house as a rental. I plan to have some long term rentals and maybe a flip here or there if the #s fit. I know this is not a very aggressive strategy but as my confidence grows (hopefully due to successful ventures) I would like to make this my full time profession. Feed back on this would be greatly appreciated! My name is Dallin btw.