Do your self a big favor. Don't wait two years, go out and get a boat now. Lots of 1-3K boats out there in the 25-30 LOA range that are easily sailable. Just looked at a 25' 1977 Columbia today going for $1,000. Has a working diesel and all the standing rigging is in good shape. Just needs a new main and a lot of interior wood work. I tell you if it had the standing room I need I would have bought it out right and as it stands I am seriously considering buying it anyway just for the scrap value.
What I am saying is, before you take the big plunge put your toe in the water. Bottom line, if you buy a boat that floats for under $3,000 you will always be able to get back what you paid for it in two years when your ready for big momma.
Dont let the dream fade or the time slip. IF your serious about sailing and doing what you state then take the first step and put some cash down. I know its scary looking at cheap boats.. Rot, old wiring and rustic engines with blisters on the hull... Of course thats not all on one boat, or one your seriously considering anyway, but those are the sorts of things that will be off on those kind of boats. The good news is if your willing ti put the elbow grease in your self, and you live within 25 miles of a Home Depot, then you can get everything you need for CHEAP AND learn how to do all the work yourself. Another benefit? Since your doing the work on a run down boat it doesnt matter if its perfect. The boat is the learning experience. Just make sure it has a good hull, good rigging, and sail. Blisters, rot all that stuff is easily fixed.
Also, you really dont even NEED to fix most the stuff. If you have rot in places or your port holes leak a bit so what? Its a starter boat meant only to get you on the water and with sailing experience in your belt. Now, disclaimer: You should NOT sail in the ocean with a leaky boat. However, Rivers lakes and other water body types that are more protected are not a big deal. The things that really bug you can be your projects and every thing you do will add experience to your arsenal and possibly add value to your boat come sell time.
Sorry for the tangent but I hate to read so many "I wanna..." post about far off dreams that easily slip your grasp if you dont take hold. Carpe diem friend. Besides, you got a trove of knowledge at your finger tips with this forum to guide you along the way.
One more thing, if your really nervous about all the big boat stuff or just don't have the money right now then join a local sailing or yacht club. Fees run around $100 a month most places and there you can get experience on small dinghy boats or even gain spots crewing on larger boats.
Read the books at night and hold fast by day. Ain't going to get salty just by eatin Morton's