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Forgive me if this is better suited for the background area, but I felt the painting section was more of the input I was looking for.

I have a decent sized collection of Dark Angels, and over the last few months have made a few models to represent the vanilla units (Shrike, Vulkan, ect) but that has proven easy to keep the general theme of my army: The Dark Angels standardized color scheme, Bleached Bone Termys, Black Ravenwing, and DA Green tactical armor (all tacticals have a robe, save for jump pack squads.)

However, Iv been wanting to dabble into a Chaos list, but I cant seem to figure out a way to make a number of the units work. Namely Oblits, Daemon Princes, and the Defiler.

The other units, such as cult units, possessed, and terminators are not an issue, as I can buy a few more DA vets/termies and make them look like the said units, but the oblits are my biggest hurtle.
What are some ways to represent the Oblits? I was thinking modified Tech Marines, or ordinance strapped terminators, but nothing seems to really click.
The Daemon Prince and Defiler I would think will come easier once the Oblits are figured out.

Any suggestions?

I was in a similar situation to yourself, i'd maxed my deathwing and ravenwing companies as well as tacticals in excess of 6000pts, and i did not know what to do, my wife of all people suggested i should start a new army, i ended up picking Chaos, and playing death guard.

I used some AOBR terminators i had spare from collecting my 100 terminators for the Deathwing over the years, i used my bitz box and some green stuff and bulked them up a bit and filled them out with heavy weapons i had spare. they turned out quite well, and i get compliments on them at almost every game i attend.

if you fancy yourself to learn some greenstuff fu, take some time and a test model and work with it. i would try using play dough etc or none set model putty until you get your skills up to where you feel confident to do your first model.

Have fun and best of luck.

As for the Daemon Prince and the Defiler, the Defiler, is a unique model in and of itself. i honestly don't use them, due to there being better options for the H.Support slot, plus i dislike the model, but i know quite a few people who make Nurgle esq defilers with the Soul grinder model, which i admit is full of win.

The Daemon Prince i have converted my fair share of them, but the best base model i can think of for a Daemon Prince with wings is the Bel'akor model GW has for order. one of which I have and use atm.

Oblits I guess you can be a little silly and just have 2 guys per base with loads of weapons

Daemon prince I believe their are conversion rules honestly all you need to do is have a beautiful model with wings on the right size base with a weapon that really stands out and your golden

Defiler.. Wow it is amazing when even I can't come up with something.. >_> Well I got nothing unless you want a dreadnaught with 4 legs with a battle cannon on it's back

The defiler I can half envision being a construct of my master of the forge, take the normal Defiler and remove the chaos items, and do.....SOMETHING to hold that look of not only a TechMarine, but the knightly feel of the DA's. Im sure with some time Id figure it out.

Diamonas, would it be possible to see some pictures of your oblits? Every time I try to envision one I draw a blank.
Now that I think of it, Servitors might work... but Id use that as a last resort.

The daemon prince, while tough, should be pretty fun. Remove the chaos emblems and green stuff or paint DA symbols on.

I wanted to keep a just-turned feel to the entire army, as I already have very little Imperial Eagle heraldry present, and any Inquisitor/DA units I had could easily be put to the side. (they where all Xeno =I= anyways.)

Try something like this:

Inquisitor in Personal Walker