Please Help me decide what to do

I had to sell my set up awhile back and am wanting to start to build a new one.

Previous set up:

Wadia 170i (only item I still have)
Lightspeed attenuator
Classe Ca-200
Paradigm sig 2's
Parasound Z dac

Signal cable silver res. cables throughout (still have these)

So I can't decide what to do. I can get a pair of sennheiser hd 700's for $450, and schitt lyr for $200, and a schitt bifrost for retail. I'm wondering if this set up will satisfy me for awhile or if I'll hate headphones compared to speakers. I've read reviews of hd700's being too bright...

If I do go this route, will the schitt lyr work well as a pre amp in my main rig later on once I build it? Will the bifrost satisfy me? I like the idea of using the lyr and bifrost together due to matching aesthetics, but sound quality for the $ is top priority.

I did like how simplistic my last set up was. 1 source, 1 power button, 1 knob for volume, no b.s., lean and mean and it sounded incredible.

I like all kinds of music and am super picky. Champagne taste, beer budget. I'm big on micro detail, resolution, imaging, tight controlled bass. I prefer a rich and warm sound over a cold dark sound.

Thanks ahead of time for everyone's help and responses!
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.