Lots of good advice here, but I'd like to mention another angle on this:
1. There's nothing necessarily "wrong" with your love letters. There's lots of good stuff there, and, although I agree with some of the criticisms and suggestions which have been brought up, I'm sure you'll have a good time if you use them as-is.
It's a taste thing, really - there's no right or wrong way to do love letters.
My preference? Provide more opportunities and choices (and less "bad stuff"), or use them to resolve things happening off-screen we don't want to watch in action (like building a wall around the compound). DannyK nailed that one, in the reply just before mine!
I'd rather start the session with some meaningful fuel for my character to follow his interests ("You've discovered one of your gang is a spy. What do you do? On a 10+, You've got her, tied up, in your holding cell. 7-9, You know who she is; but she doesn't yet know that her cover has been blown - you have an opportunity, if you act quickly. 6-, She knows she's been found out, and she's ready for you (two of your best guys have gone missing, by the way)").
It's only really appropriate, I think, if something was already in action, and you want to disclaim responsibility about how well it's gone. (For the above example, maybe the session ended with you saying, "Hey, Bran: apparently, someone's been leaking your plans to the hardholder," and the player, "Ok, I put my best men on it...") That doesn't involve the character directly, and you don't want to spend playtime on it, nor do you have a ready idea for "how it should go", so rolling for it settles it nicely without you having to do that.
I also find that roll+stat isn't always right for this; sometimes I prefer to work in some choices for the player.
("Roll two dice. Who is going out? Toyota is the best person for this job, but he's still got a concussion. Do you put him on it, or let him rest? Also, they might need transportation.
* If Toyota's on it, add 1 to your roll.
* If you're willing to lend out your truck for the mission, add 1.
[...]")
2. A love letter doesn't need to follow a "roll+adds" system. You could do something else entirely, like just having the player choose from a list (no rolling). Or you could ask them some questions, instead.
For instance:
"The battle with Tum Tum's gang was a rough one, but you came out of it ahead, thanks to the hardholder's help. (For which, remember, you promised to send him one of your soldiers - but not just one of them, one of them who could read and write.) Some of them got away, but you also managed to take one of theirs alive.
Whom did you capture? Choose one. The other got away.
* Tum Tum, himself
* Tum Tum's lieutenant, the one who knows the codes
Whom do you send to the hardholder, as a way of saying thanks? Flasher - the one you were planning on sending - didn't make it out alive, unfortunately. You've only got two other people who can read; choose one.
* Toyota is your strongest and most reliable: she'll serve him well, but she doesn't like him, does she?.
* Dremmer can read, but he's getting old, weak, and he's a drug addict."
I like this kind of thing, because there are tough choices which save us the trouble of establishing those details early on in the session. When we start play, this player has a clear starting scene/position: they have a prisoner to deal with, and they can think ahead accordingly. Similarly, the hardholder will be presented with a less-than-ideal candidate, and you can see how they react, and start building that PC-NPC-PC triangle as you begin the session. Both present a good starting scene for that character.
You can just prepare provocative questions, too, to jumpstart the session:
"Last session, we left off with you, alone and unobserved, in the hardholder's "precious items" depository. You could easily steal something small, if you like. Ask the hardholder's player to tell you about three special, memorable items she keeps down there, and what they mean to her. Do you take one of them? And, if so, why? Did the hardholder take something from you, way back?"
(Ideally, this kind of thing ties into their Hx or builds on other themes you find interesting in their relaitionship. Obviously, this would be no good if you expect the player to say "Nah"; you have to build on established relationship dynamics to make sure it's relevant to the players. I would only use the above if the player had showed an interest in stealing something earlier in the game, but it so happened we didn't get a chance to discuss it in detail.)
It's great when, as in this example, it encourages the players to talk to each other.
If you send them out ahead of time, you might get some more interesting or thoughtful answers, too.
Not the best examples, sorry - but the point is that I encourage you to "think outside the box". A love letter doesn't have to be a "roll+stat, on a 10+ you get a good thing [...]", etc.
Start-of-session moves for some of the characters (especially the hardholder) might also be a little overkill if paired with a love letter, so choose appropriately. My general rule of thumb is that those moves (which were chosen by the players!) are the source of trouble, and the love letters, instead, are a source of opportunity. (Of course, if a character is all comfy and cozy, and has no start-of-session moves or problems, it might be a good time to provide an opening for such.) But don't forget about the start-of-session moves when you write your love letters!