Suggested entry path into vinyl...

If you start with 0 LPs and 0 vinyl rig, right off the bat you have a decent-sized expense ahead of you. However, given the first sentence of your original post, the money (within reasonable limits) will not be the most "expensive" bit about jumping into vinyl. The "expensive" bit is the time spent looking for vinyl, fiddling with your system, reading about how to make it better, and eventually the vinyl itself. If you buy the gear used, and decide a year later you do not want it, you might take a small loss but not much of one. The other stuff (the Fremer DVD, the brushes and cleaning fluids, the time spent, etc) will all be more expensive.

I find vinyl playback to be enjoyable, but am not religious about vinyl being "better than digital." I use vinyl to discover music. I can buy lots of decent records for not much money, discover what I like, throw back the rest, and then I can go learn some more. I can also listen to what I have found. To a large extent, I do not pay lots of money for a great pressing in order to get a great original pressing of something I already have on CD or SACD. If I can find the record for $5, I might buy something I already have on CD.

Personally, I would recommend that you 'experiment with vinyl' in a completely different way. If you have garage sales or thrift shops in your area, I would try to find a used working Dual, Thorens, or other table from the 1970s or 1980s. If you buy a used cart (or spring for a new one) which matches the arm, you will get a lot of the subjective qualities you seek out of a $50 yard sale special and a $300 cart which matches (ask here or over on the Vinyl Asylum at Audioasylum.com for what would match). If you really want to go cheap, try a decent receiver from the 1970s at the same yard sale and you might find an acceptable phono stage. If after buying some thrift shop records, cleaning them, setting up the table, and setting it up again, you find joy in listening to the records you bought, and joy in finding more music and playing that, then the vinyl experience is for you and you can sell your garage sale finds at a garage sale and move up to a more expensive set-up.

Thanks Samhar and T bone. Appreciate the thoughts.

i have to say T bone's sugestion, is one as if to say, don't bother you won't(i don't) think it is any big deal and you won't like it anyway! WRONG! Vinyl is more then just the music, it is a obsession, it is a hobby, it is involvement in the music, it is a conection to the music, it expands your taste into band you would have never heard before, it is an investment, and when done right, it is GREAT sounding music! it is not for everyone but if it is to your liking it can be an adiction that can't be kicked. the bit of good advise he gave is to start used. i found vpi's a great starting point, but buy the best you can afford and are comfortable with spending. there is a lot of great new and used vinyl out there and more every day. i buy originals. rarely do i buy reissues, first issues usally are the best sounding and the most collectable. so if you chose to take the plunge good luck and enjoy the jurney. i have had a great ride up to now and plan to continue for many years to come.

I don't know how you got "don't bother" from T-bones post. I think his approach is the more down to earth one.

Original pressings aren't always the best. Mastering and cutting techniques improved over the years (I not sure about the present. I think a lot of that expertise is gone forever.). And you can find some deals by getting later pressings that aren't on some audiophile checklist.

Koegz, I certainly did not mean "Don't Bother!"
I completely agree with you when you say

"Vinyl is more than just the music, it is a[sic] obsession, it is a hobby, it is involvement in the music, it is a conection[sic] to the music, it is an investment, and when done right, it is GREAT sounding music! it is not for everyone but..."

What I meant is that the "bother" is actually far more of what vinyl is than the making sure the $2000 budget is spent just right, and whether this $600 phono stage smokes that $795 phono stage. Within a $2000 budget there are literally hundreds of ways to get it right. However, none of that matters without the commitment to do all the other stuff. As you say, it is an obsession, a hobby, an involvement in the music. It is also an involvement in getting up and changing sides every 20 mins, and brushing the records, and cleaning the stylus, and cleaning the record when you get it, and putting it in a new inner sleeve, and making sure your albums are stored right, and protecting the jacket bottom, and making sure your VTF hasn't drifted because this one is a thicker vinyl, or you changed mats, and cleaning the stylus again, or cleaning the record again (not to mention learning about how to do all this stuff).

If one has zero dollars invested so far in equipment and vinyl (except for the Mikey Fremer DVD on its way), to me the risk is on the "doing the vinyl thing" aspect rather than the "owning gear" aspect. If one can get involved with vinyl with a light heart and open mind, that is a good way to avoid the stress of "I've got $f&6#@ invested so I'm damn well gonna appreciate vinyl!" One can ALWAYS spend more money later. As for reissues vs originals... for someone just getting in, anyone should be able to enjoy well-pressed/engineered reissues. Many of them are indeed very well-done. They may not be collectable, and if you listen to ten great reissues vs their 10 great originals, the originals may be better in every case, but I agree with Daverz in that that is where the deals are, and ten great reissues is ten great pieces of music with the ability to go out and buy dozens (or hundreds) more for the same price as the ten great originals.

In any case, if Cmalak decides to splurge on gear at the beginning, used is still the way to go to get the best bang for buck.