Please Help me decide what to do

You have to live with "phones for a few months to see if that's all you need.
You can buy a headphone system for $1500 or less that is better than most 10K speaker systems so the risk is much less.

Thanks Schubert!

Okay, I'm all over the board here. I guess I should have givin a budget; I'm thinking $1,000-$1,500 total for now.

Gear I am considering:

Peachtree I Decco with level 2 mods from underwood ($829)

Benchmark Dac1 ($700)

Emerald Physics 100.2se ($700)

Sennheiser hd700 ($450)

Signet sl 280 bu

I was thinking that the Benchmark Dac 1 might satisfy my needs for a Dac/Preamp indefinitely. I could pair this with some Sennheiser HD700's and possibly be content. Another option would be to pair it with the Emerald physics amp and Signet sl 280 bu speakers...

I like the idea of the I Decoo but I am afraid that it wont be enough, even with the mods, and I feel like the amp, preamp, dac are all mediocre so when I did start to upgrade individually, the I Decco would not be of any use.

I figured that the Signet sl 280's would be decent for the $ and would actually sound as good as most of my other options under $600 (mostly local speakers on craigslist or used vendors). I really fell in love with my last Paradigm Sig 2's with beryllium tweeters and I know that in order to get something similar, I'll have to spend $1200 or more, which I don't have right now for speakers.

Anyways, still confused and looking! Please give me some more input! Thanks!

You're over thinking all this.
A peachtree whatever with DAC + used Sennheiser 600's will either do it for you or not.

lol, I overthink everything Schubert. It really is difficult being me.

I have been beating my head against a wall for the past 24 hours trying to figure this out.

That I Decco with level 2 mods is $830, for $1100 I can do a nova pre and nova 220...

Decisions decisions.

I also checked out Head Fi for some sort of direction but that site is laid out horrible compared to Audiogon.

I have access to some HD700's for $450 or some HD650's with Cardas cord for the same, $450.

There's also some speakers in my area that I've been looking at: Totem Mites ($400), Obligatto Legato ($485), Linn Ninka ($500), Krix Lyrx ($500), Focal 806V with stands ($535)

I'd take the 650 with cardas cord.

I heard master and dynamic phones the other day at stereo exchange in nyc for the first time of a nice Rogers set. Nice product that I had not heard of. I've auditioned many phones recently and those were worth a second glance someday.