[OOC: As can be seen here, divine casters are not commonly available in this campaign for setting reasons (i.e., Magudonya is the 'world of mages'). And even though Midian is part of a religious organisation, the priests of that organisation are all based around the arcane character classes. While I am certainly willing to entertain the idea of a player's character gaining access to a divine caster class at higher character levels, that won't occur at second level. It would also necessarily be as the result of some sort of campaign-based quest.

Having said the above, perhaps a more worrying progression choice is Warlock. If Midian were to take this path, it would likely bring him into direct conflict with the organisation he is currently working for—and possibly be at odds with being a cleric whose powers are god-given—because of the supernatural connection between a Warlock and their patron. Also, this relationship is something that would need to be developed in play. For example, Midian might find a book that might get him into contact with a Warlock patron from this campaign world (e.g., Killrellian).

I'm not saying that your idealised character progression can't be done, just pointing out that it will be difficult to do in this campaign because of the setting. Also, with the limitation on cleric, what would be your proposed second level advancement be?]

OOC: Bard would be the easiest choice to get into more skill access faster. 

[In that case, what I'd like to propose is that I change Midian's Innate Sorcery feat to Magic Initiate (Bard) with the spells See the Arcane (which he already has), another cantrip of your choice and a 1st level spell of your choice (with the choices not being ones that might have affected previous events). This is to represent his previous training in the arcane that he would have been undergoing as an apprentice Seeker. At second level, you can then multiclass to Bard to get access to the full Bard capabilities. If you want, you can also nominate a musical instrument for him to become proficient in. Though I don't considered that a necessary aspect of a Bard, as can be seen with my Tyrus character.]

OOC: I think that’s a good plan. I can also go in favor of setting flavor over “skill completionist” and just plan on rogue/bard as adding cleric and warlock does require jumping through some narrative hoops. I’ll just select four skills I can do without in the overall plan. 

Quote from Izraal1 >>

OOC: I think that’s a good plan. I can also go in favor of setting flavor over “skill completionist” and just plan on rogue/bard as adding cleric and warlock does require jumping through some narrative hoops. I’ll just select four skills I can do without in the overall plan. 

[OOC: Any thoughts as to the other cantrip and 1st level Bard spell you would like him to have at this stage in his career as a Magic Initiate (Bard)?]

Midian takes his time as if saying a momentary prayer to Donai in order to linger and eavesdrop for a moment, then excuses himself, returns to his room to change to less conspicuous clothing, and then he will head out to The Compleat Sage Bookshop, conveniently in Scholar's Ward where he had been intending to ask around about Moonson.  

[OOC: Do you want to have Midian use the 'wardrobe' facility of the Seeker's quarters that I mentioned earlier? If so, make the Deception check at Advantage to give me a baseline for how people initially take to Midian when they see him. Less than 8 will be considered a failure for experience points and less than 5 will be an obvious failure and will allow a new attempt to be made. ]

OOC: Yes, apologies, I will move forward at present and save mechanics brain storming for a later time.

7 Deception with advantage 

Re roll for exp 23

[I have increased Midian's experience.]

Midian's time in the 'wardrobe' certainly end up with him not looking like an apprentice Seeker of the Temple of Donai, but as to whether he has achieved the desired effect he is a little less certain about.

[OOC: Out of interest, did you have particular appearance/disguise in mind? Also, when he leaves the Temple, what weapons, if any, will he be taking with him. Knowing his Bard cantrip and spell would be helpful too.]

Quote from phillberrie >>

[I have increased Midian's experience.]

Midian's time in the 'wardrobe' certainly end up with him not looking like an apprentice Seeker of the Temple of Donai, but as to whether he has achieved the desired effect he is a little less certain about.

[OOC: Out of interest, did you have particular appearance/disguise in mind? Also, when he leaves the Temple, what weapons, if any, will he be taking with him. Knowing his Bard cantrip and spell would be helpful too.]

 Probably “Friends” for the cantrip. On the disguise, the intended disguise would have been as a scholar, possibly a university student to fit in as his investigation is taking him to the Scholar’s Ward area. He likely didn’t nail the look but he doesn’t know that. 

[OOC: I have changed the extra feat to Magic Initiate (Bard) and added the Friends cantrip. However, for some reason, D&D Beyond is not letting me add my homebrewed See the Arcane cantrip to your character even though I have added it to many characters in the past. I am looking into this. 

First level Bard spell? And weapons he is carrying when he leaves the Temple?]

[OOC: Midian now has the See the Arcane cantrip on his character sheet, which I added by also giving him the Innate Sorcery feat as well as the Magic Initiate (Bard) feat. I suspect the problem is because his actual character class is Rogue and the spell isn't accessible to that class in its published form. This problem should go away when/if he actually picks up a level in Bard, at which point, I will be able to remove the surplus feats from the character.]

Midian takes the two daggers, his thieves tools, and wears his leather armor, as he heads out to the Scholar's Ward, dressed as a young academic, or so he believes.

OOC: Thank you, it all looks updated, I will still need to select a level 1 bard spell it seems.  

Here is a mockup of the current planned course for the build, in theory at least.  Not all skills covered, but sufficient to make him a skilled investigator/social manipulator character.

https://ddb.ac/characters/28865948/1joMqQ

[OOC:

It will be interesting to see whether the character develops as planned. Speaking of which, any thoughts about his Bard spell? Bane would be my suggestion. It could be really useful for getting out of a tight spot if caught while spying and the spell component (i.e., a drop of blood) is fairly easy to come by.

I have moved some things about on Midian's character sheet to represent your instructions above. I have also added a few things, such as a coin purse to his carried equipment and a lute to his other possessions; it was on his finished sheet and he can be learning to play it now. 

I will assume Midian also takes time out to eat while he is in the Temple and so he is heading out back towards the Scholar's Ward a little after the first candle call of the afternoon (i.e., ~1pm)

]

Adjusting his borrowed scholar's robes so that they conceal his daggers and cover as much of his armour they can, Midian heads out of the Temple heading towards the Scholar's Ward. 

As he heads north across the city he can still hear the candle callers in their secondary role as town criers announcing the king's decree, and he can't help but notice the groups of people in the street talking animatedly about the king's decree.

[Make an Insight check to determine the city's general response to the decree. Less than 7 will be considered a failure for experience points.]

Insight to read the mood of the city: 17

OOC: He would probably opt for the general usefulness of Healing Word if that is an option. 

[OOC: Healing Word is fine. I have added it to Midian's character sheet.

As I did this, I noticed you changed his starting feat and ability scores, which breaks continuity as he has used his Mage Slayer feat already in play.

I assumed you were going to implement these changes during his character development, not retcon the character.]

As he moves through the city Midian gets the general feeling that the response to the king's decree is split based on race; where it is groups of Sorians talking, there is general—if guarded—agreement, whereas, for the larger Stemian population, the groups of people seem to be either complaining or confused about the sudden change in policy.

Once across the bridge into the Scholar's Ward, he heads towards the Compleat Sage bookshop, the location of which he remembers from his search of the area this morning. It wasn't open then, but it is now; the door open to let some light into the small shop seemingly crammed with bookshelves full of scrolls and handcrafted books.

Midian enters the shop and has to wait for his eyes to adjust because the light from outside seems to be the only illumination in the shop.

[Make a Perception check.]

OOC: Correct, given the nature of a one on one game, it seems having a broad array of skills just makes more sense than combat optimization. I would be fine with keeping the original array and feats and switching during some story transition alternatively, after a major milestone, etc. I will wait to apply the bard future mc features until a later time. 

16 Perception check 

OOC: If my assumptions considering the rebuild of the character were incorrect, let me know and I can switch back. A skill heavy character seems a better fit for the somewhat unique format of a single player game, having experienced a bit of it. 

[OOC: It was just something of a surprise, is all. Happy to run with this build as it is still in following with the basic idea of the character. However, as with the last version, I am going to need to add 1 to one of your mental abilities for campaign reasons. Your choice: Intelligence, Wisdom or Charisma?]

There are windows in the shop's front but the shutters are closed, and in fact, they don't look like they have been opened for a very long time.

As Midian eyes adjust to the gloom he can hear the sounds of someone moving about coming from the back of the shop. He is also surprised to see a sudden movement at floor level and notices a large rat looking up at him from about fifteen feet away.