Considering analog...but nervous

Well, I've been here before. Once again, I'm thinking of venturing into the Analog world, but before doing so, I wanted to pose a few questions to fellow agoners to make sure my head (ears?) are in the right place.

Some Background: My current setup consists of a Modwright Transporter, Musical Fidelity KW 500 (hybrid tube pre/SS Amp), and Focal/JM 1027be speakers. My entire current collection is digital and I have NEVER owned Vinyl before NOR have I ever heard a high-end Analog setup.

My Tastes/musical likes: I am all about soundstage and imaging. Vocal accuracy is hugely important and instrument placing (hence, imaging) are part of what I look for when listening. Genre wise, mostly rock, folk, acoustic and blues. Some jazz as well. I generally try to stick to labels that produce good-sounding material...not over-compressed garbage.

On with the questions:

1. One of the biggest things that has kept me from trying Vinyl thus far is the concern of excessive hiss and crackle/pop that vinyl is known for. Is it safe to assume that purchasing new Vinyl and played on a higher quality setup will reduce (eliminate?) the pops and crackle sounds? I have no problem purchasing exclusively new vinyl, knowing full well that the process of shopping used is what draws so many to this market...

2. If I purchase new vinyl, only play it on a decent player, and store it properly, will I still have to clean it? How expensive is a cleaning machine? Are there (reasonable), less expensive alternatives to a cleaning machine?

3. Based on my integrated (tube-pre,SS amp) and speakers, are these a good match for Vinyl? Does anyone know if the KW 500 Phono input is adequate for a good turntable? My digital system has a tendency to be on the bright side for a lot of material, but not everything. Strangly, even at 31 years old, I can still hear up to around 19Khz so I'm a bit picky about the highs...

4. How complicated is the setup of the TT? Being that I've never worked wtih it before, I'm somewhat intimidated by the "setup" requirements of the equipment. What are the core requirements/knowledge to properly setup a TT.

5. And finally, the most subjective question of all. If I had a budget of about $1,000-$1,500 for a TT, Tonearm and Cartridge, what would be a good starting place? I'd obviously be looking for used here from Agon.

I know this was a long post so thanks for hanging in and reading it all :-). Any feedback would be greatly appreciated.

-gh0st