If you love the game enough (and it's an amazing game, so you SHOULD) you'll be replaying is so many, many times that concerning yourself over "which should I do, first?" won't matter in the long run. Since FONV contractually follows the same broken model as FO3, there's a schism between events in DLCs and events in the main story, however Obsidian did take the time and had the foresight to include SOME level of callback to your decisions in the DLCs with characters and events in the Mojave. Your level of attention with certain NPCs will impact your available choices in "Dead Money". If you've met Caesar before starting "Honest Hearts", that can be addressed. What you do in "Lonesome Road" will directly impact the Mojave. "Old World Blues" is about the only one that doesn't have ANY direct ties to the Mojave in the same way the others do, although it does provide some insidious backstory, and the events you uncover are somewhat of a twist, so it's still not bad, or vacant of importance. Most importantly, every DLC ties in to each other, at least as far as story and plot are concerned. "Lonesome Road" doesn't ignore that events set in stone in "Honest Hearts" ever happened, it acknowledges this. As does "Dead Money" and "Old World Blues". They all tie in quite well with one another.
For balance purposes, I'd say engage the DLCs in the following order: HH, DM, OWB, LR, and the story importance will also benefit from tackling them in this sequence, as well. Consider LR the ultimate finale of the game, which technically should've BEEN the end of the game, but for various reasons (again, contractual obligation to follow that crappy FO3 model and time constraints) it isn't. HH provides some nifty backstory to many characters you otherwise wouldn't uncover if you stayed in the Mojave. DM is dark and creepy, and it won't hurt to tackle it as early as you finding the "entrance" to the DLC for the first time. OWB is at once goofy and dark with some stunning revelations, although it and LR share an irritating commonality that the enemies are STUPIDLY powerful, so hit those second to last, and last. You won't miss much if you leave them both for later, and although you won't miss much if you complete each DLC in ANY order you prefer, it might feel most natural in the order I suggested. They may lose their impact if you wait until you're Level 50 to begin them, likewise you'll miss out on a HEAPING load of many Perks and useful treats from the DLCs that you could put to great use in the Mojave if you don't visit them earlier. DM can be completed with ease if that's THE first thing you do when you leave Mitchell's house, and HH's main story won't pose much difficulty if you do the same (although ONE of the side quests will prove difficult unless you're decently leveled and geared up).
As soon as you feel like you'd be interested in seeing something new, feel free to start one of the DLCs. There are no time limits on any of the quests (which I think is a bad thing, but hey, that means no drawbacks to leaving quests unattended while you adventure beyond the Mojave) so "when" you ought to begin whichever DLC of your choice won't matter at all.
