Can someone point me in the right direction? LP player / Preamp / Dragonfly Red...

If your Sony has a phono stage, keep and use it. If not, add a Bellari tube phonostage ($350). No real need to discard the Sony!

Sony is a cheap STR-DH100 but it actually sounds pretty good.  I have the volume set to 50 and control the output via my computer.  I let Audirvana and DragonflyRed do all the SQ stuff. 

I have to beleive that the Onkyo Int would make a big difference in my sound.  Just hard to drop $400 when my setup sounds pretty damn good right now.  But I want a TT and that changes things...  

I actually prefer the idea of getting the AT-LP120 and upgrading bit by bit.  I know I would spend more over time but its easier to hide from the wife!  ;)  The Pro-jec Debut Carbon has great specs, but am not a fan of the look...  And to get a mint Technics 1200 would be like $1000+ so probably not going to work for me.

Researching if there is even a way to "input" Audio into my IMac 27" 2012 at all anyways.  I thought I could but not sure now.

If your Sony has a phono stage, keep and use it. If not, add a Bellari tube phonostage ($350). No real need to discard the Sony!

No phono stage on the Sony.  I will check out the Bellari - thanks!  At 350 though, its almost the Onkyo Int. which has the phono stage and LOTS of other SQ enhancing features.  

I guess there really is no point to running the Vinyl through my Computer to increase SQ via the DAC if I get a descent amp with a Phono stage right?  Especially if I have to buy converters and gear to do it?

Guess I was hoping for a shortcut to afford a TT now and get good-enough sound that I could upgrade later.  :(

I’m in agreement with those suggesting vintage gear. But, be forewarned that some of it, especially Technics SL-1200mk2 turntables are pretty much all thrashed by “dj” rappers. I know from my experience, I wanted the higher end SL-1700mk2 on which the 1200 is based. They are extremely rare in any condition, so when I saw one for sale a few months ago, I jumped at the opportunity. And yes, it was owned by a wannabe “dj” rapper that kicked the living £#£}¥ out of the poor thing. Determined, I bought it and set out to restore it with a new plinth, tonearm, Audio Technica VM540ML cartridge, mat, and 1200 feet and dustcover. It turned out very well, and I’ve got it connected to a customized NAD PP2 phono stage (upgraded 2 amp regulated power supply of my own design, and soon to get a Burson V6 Classic Duo discrete op-amp), pair of vintage NAD integrated amplifiers (3020i and 3225PE) in a bi-amp setup driving a pair of Energy Reference Connoisseur speakers. 

The whole system cost me around $2000,
and equals or betters performance of new systems over $10,000. You can do this also, with the same or similar gear. It will only take time and perseverance to set your goals and be on the lookout on Kijiji, EBay, etc...  for viable gear. 

Try Schiit Mani if you want good sounding, good value phono preamp. Pair with Nagaoka mp110 cart. Mani is 140 bucks including shipping fron Schiit Audio. Nagaoka cart about 120 bucks.