Writing Quality: Meh, it's alright. There are a few grammar issues, and the formatting could be done better, but it isn't actually bad. Getting a native English speaker to edit chapters before they are posted would help.
3 Stars.
Stability of Updates: Pretty frequent, no set schedule, but not bad by any means.
4 Stars.
Story Development: Forced. I think that's the best way to describe how the story has gone so far. We are introduced to a self-insert with a system. Standard stuff, but pretty much immediately we end up at high-school. We don't see any initial struggle to gain power a world as unstable as DXD. We don't see any character development from growing up with a new family. We don't even get flashback snippets of training. Just a time-skip straight to high-school. As a result, the reader has no idea what to expect from this new Issei, and if you are like me, are sorely disappointed by how he acts when he KNOWS how much trouble he will be encountering.
Furthermore, this new and "improved" Issei is railroaded completely onto whatever "plot" the author is going for. We know that in canon Issei chooses to go to Kuoh Academy because it just became co-ed, this Issei could've chosen literally any other school nearby and wouldn't have to deal with any of the crap associated with the two devil heiresses. I don't have a problem with Issei going to Kuoh necessarily so long as there is a valid reason provided. We get no such reason. Issei in this fic is a powerful, self-proclaimed coward who doesn't want to get involved with the things canon Issei was forced to deal with. So why in the world would he CHOOSE to go to Kuoh when given the choice? The reason is never given to us, so we don't know.
Even worse, this new Issei should've had YEARS to think of a plan to deal with the heiresses should he be exposed. He should've KNOWN that eventually he'd be dragged into the supernatural world, and had a plan for that. But no, we're given an Issei who has no idea how to talk to girls, is cowardly, has no plan whatsoever, and is still somehow ranked #1 in his division of school. It makes no goddamn sense and is lazy writing at best.
Then we have the fact that Issei cannot use the power he trained for, for whatever bizarre reason, and the end result is that the author is just going to do whatever he wants.
1 Star.
Character Design: Lacking. The characters made by the author, SI Issei and "Lina-chan", are less fleshed out characters and more like a set of loosely defined character traits. As I said earlier, we are given no real character development for Issei, he just ends up at high-school and have to deal with his actions from there. MC Issei is a coward, top-ranked student in his section of high-school (therefore should be somewhat intelligent), and just wants to live his life. That is how he is described to us as a character. So how does that translate into his actions? It doesn't translate at all.
One of the first major actions Issei does as a character is to fully expose his power to Sona, and demand that she become his woman. First off, where the hell did this confidence come from? Secondly, in what world do you think exposing yourself to someone you've known for all of 2 damn minutes is a good idea. Thirdly, you've been told by "Lina-chan" that you cannot use your power, so why in the Hell would you ever paint such a huge target on yourself? It's forced, it makes no sense given what (little) we know of the character. My major issue with all of this is that there is no plan. He's had years to think of something to do, and all he came up with was "avoid stuff", and then he fails to do even something as ****** as that.
1 Star.
World Background: It's pretty meh. DXD canon is a fully fleshed out world, and the additions added by the author haven't broken anything.
On the other hand, nothing of significance has been added. There has been no real explanation or examination into the nature of the supernatural powers added. The system is poorly explained, and the details about how it works were never really established. Normally, you'd want to at least examine some of the aspects of the system granted, but nope. The same could be said for "draconic power" whatever that is. Overall, nothing that has been added into the story has been explained. That's not even counting how "Bahamut" A MACHINE could fuse with Ddraig. I let that go for the most part as author fiat, but dammit at least give a seemingly plausible explanation.
2 Stars.
Summary: A stereotypical System SI novel where the author has no real idea what they are doing, and no real plan for what's going to happen other than what girls are going to be in the harem. It feels like something my 12 year old cousin could have written given a few hours of time to spend on a computer.