While Luna would normally allow a new hire to make their own way to their job as a first test to see how well they would handle themselves. However, the current situation called for her to escort Walter to his new occupation for a number of reasons. First off, after the splash Alucard made when he was 'recognized' as Luna's legal husband, having another human - or at any rate, what would be mistaken for 'another' human by the populace - was simply asking for trouble, and not the sort she could enjoy as free entertainment. Second, given the reputation Alucard had in Ponyville from his few appearances there, sending Walter in alone to find his way around without an official introduction would also be just asking for trouble.
The most important reason, however, was Luna's thoughts after seeing a demonstration of Walter's combat skills and his proposed route - on foot - in order to avoid causing undo civil unrest. As dangerous as some of the monsters of the Everfree could be, there was no reason to depopulate it needlessly.
As such, the chariot came to a discreet halt just outside Ponyville, allowing Luna and Walter to disembark quietly and make their approach. As she'd instructed, Walter took the lead while she walked behind, ready to step in if necessary. Much to her surprise, their first encounter was with her daughter's new familiar, and a meeting that apparently made Walter feel awkward.
"Guten Tag, Walter," Jerry greeted happily. "Did you get reincarnated to be with the ponies, too?"
"In...a manner of speaking," Walter allowed awkwardly. "I have been hired to be...I suppose the best way to put it would be Scootaloo's Governor."
Jerry raised an eyebrow. "Somehow I don't think that will be going over well." The catboy grinned wickedly. "Should be fun to watch, though."
"I'm pleased you find it so entertaining," Walter observed dryly. "And where is the young Miss?"
"Playing with her sister," Jerry allowed readily. "Which is why I'm not."
Walter sighed ruefully. "Seras can do so much better for herself..."
"And what makes you think you get to say who's 'good enough' for me, ya wanker?" Seras demanded angrily as she flowed into being out of a cloud of red and black. "Speaking of that, what are you even doing here? Wasn't Dad going to, what was it-"
"Can we do without the crude language, Miss Victoria?" Walter asked in a pained tone. "I'm here to offer young Scootaloo a consistent, stable, rational parental influence. I'm pretty sure getting those around her to watch their language would be a good start."
"You? A good parent?" Seras demanded dismissively. She then paused. "Actually, aside from the whole turning traitor thing, I can see that."
"Wait, what?" Luna demanded in confusion. "Alucard didn't mention that when he recommended you for this job."
"He didn't?" Seras, Walter, and a French ghostly voice asked in shock.
"He probably wanted to watch this unfold," Jerry observed playfully.
Seras sighed. "Yeah, that sounds like him."
"Where did that other voice come from?" Luna demanded in confusion.
"Oh, that would be me," the voice spoke up, seeming to originate from somewhere around Seras...specifically, in the black and red miasma that was part of her being. "Enchanté, mademoiselle. You may call me Pip."
"You know how Pops has a few souls inside him that he carries around for various reasons?" Seras clarified. When Luna nodded, she jerked a thumb into the miasma. "I've got Pip. There was...a rather significant moment when I first drank from a living being, and since I had his permission with his dying breath, he tagged along for the ride."
"And what a ride it has been, ma chère," Pip observed playfully. "Though your recent choices..."
"Hey, I told you why we weren't going with your suggestion!" Seras snapped. "Your soul along for the ride or not, it would have felt too much like twiddling to me!"
"So instead I am along for the ride to have anozer man inside my lady?" Pip demanded angrily. "Not to mention experiencing it myself."
"Oh like you've never wanted a threesome before!" Seras countered dismissively.
"My idea of a menage trois normally involved anozer woman."
"Aren't I enough woman for you?"
"More than enough, ma chère, but zen I do not have you all to myself, do I?"
"Keep in mind who Pops is."
Pip sighed ruefully. "So suck it up and learn to enjoy it?"
"Exactly," Seras confirmed. "Also, get out of my ass."
"But it's so comfy!" Pip complained.
"Don't I know it," Jerry purred.
"I see why you wanted someone somewhat responsible," Walter observed ruefully.
"...I hadn't realized it had gotten this bad," Luna murmured in awe. "I'm left wondering how Scootaloo is handling-"
Walter suddenly jerked his hands and gave his fingers an odd twist. Light flashed in the air, and Scootaloo was suspended in a net of silver threads to one side of him, her teeth inches from his neck. "Dammit, sis!" Scootaloo complained. "You were supposed to be a better distraction, not get distracted yourself!"
"Oh, like it's my fault Walter's powers are bullshit?" Seras demanded angrily.
"Seras!" Luna snapped angrily.
"Dad's words not mine, but they're true!" Seras complained. "So lay off, Mom!"
"So is this misbehaving, or training?" Walter asked Scootaloo calmly.
Scootaloo tilted her head thoughtfully. "Hmm...depends if Mom is watching or not?" she asked innocently.
Walter chuckled ruefully. "Tell you what. If you agree not to actually drink from me, then it will only be misbehaving if I catch you before you get your mouth around my neck. Otherwise, it's training. How does that sound?"
As Scootaloo grinned from ear to ear, Luna lowered her gaze and sighed. At least he's good with children, she mused ruefully. Still, I wonder how he'll-
Walter's other hand jerked and he twisted his fingers. There was a whistle in the air and Apple Bloom, Sweetie Belle, and what looked like an arcane bazooka that had been built in a garage from scrap were also suspended in the net of silver threads, though held more gently. "...does that weapon actually function?" he asked, his eyes on the barrel.
"No, but that one does!" Sweetie piped up as her horn glowed.
A blast of confetti exploded all over Walter. "...a...party cannon?" he asked carefully as he set them down to brush himself off.
"We borrowed one from Pinkie!" Apple Bloom declared happily. "Gotcha!"
"Let's check!" Scootaloo declared as they all turned to look at their flanks...which remained blank. "Aww, no Vampire Hunter Hunter Cutie Marks."
"What would that even look like, anyway?" Sweetie asked curiously.
"Other than confusin'?" Apple Bloom clarified.
"Probably awesome," Scootaloo pouted.
Walter finished brushing himself off. "You are planning on cleaning this up, yes?" he pressed holding out a broom and dustpan sized to the fillies.
Luna chuckled as she watched. It seemed Walter was as unflappable as Alucard had stated. Perhaps things would work out alright after all.