Wendy finds Jennifer, and alerts Hoffman, and has her moved to the orphanage?

There is a gap of about a month and a half between the time that Jennifer escaped from Gregory’s house and her arrival at the orphanage. Considering that this time-gap was during a what was probably a snowy time of the year in that part of England, I doubt that Jennifer would have spent much of that time out of doors. In my imagination, Jennifer got into a condition of poor health due to malnutrition and cold temperature before she ever left Gregory’s basement, and Wendy was motivated by that to press harder that Jennifer should leave the basement. Then Wendy led Jennifer to a hospital (or perhaps to a police station, from which they would have sent Jennifer to a hospital), but didn’t herself go in with Jennifer (so as to avoid questions that would be troublesome to answer). Jennifer made up some story that wouldn’t draw attention to Gregory. Then, once Jennifer was recovered enough, she was sent to the orphanage. This is largely conjecture, but I think it makes sense. I don’t imagine that Wendy brought Jennifer to Hoffman. I think that both Wendy and Jennifer would have wanted to have Jennifer become “found” further away from Gregory’s house, so as to avoid implicating him in any way.

There are unused sound files that depict the first impression that the other orphans had of Jennifer was that Jennifer was “really scrawny”. I think this may support the idea that Jennifer was malnourished as a result of her stay at Gregory’s house.

Wendy writing in July “I am so relieved that you are well again!” may indicate that Jennifer was a long time recovering from her stay at Gregory’s house and that she was ill when she left there.

The airship took off April 25, and Gregory’s first diary is June 1st. Are we to assume that in between that time period of a couple months, the shipped crashed then? Because the entry in which the airship is noted as missing doesn’t occur until June 23rd, but since Jennifer has been living with Gregory for some time now by this news report, we know that the airship has already crashed, or else she wouldn’t be living with him. Right?

I think you’ve got it wrong with most of what you’ve written. Read my blog-post When Did the Airship Crash? and I think it will clear up a lot.

And then, Wendy finds Jennifer, and alerts Hoffman, and has her moved to the orphanage?

‘Cause love itself is… just as innocent as roses in May.
And it’s pure white… just like sin.

Prior to June 1929 everything was fine and Jennifer’s life was unsullied by Gregory and the Aristocrats.

Martha died after Hoffman decided to leave.

In the “Once Upon A Time” chapter, Jennifer tells us (at the portrait of Hoffman in the foyer): “One day, Mr. Hoffman suddenly disappeared. Clara and Miss Martha soon followed, leaving me and the other orphans alone.”

~
Lexzl wrote (of the letters between J and W):

January comes between October and November.

See my blog-post: An Incorrectly Dated Letter From W to J

~
Lexzl wrote:

the months you play through have NOTHING to do with documented months

“NOTHING to do with” is a bit of an overstatement, I think. Usually there is at least some tiny connection somewhere that can be found. But I agree that the months ascribed to chapters are not, as a rule, reliable indicators of how to date elements within the chapter with regard to Jennifer’s forgotten past.

[Hoffman's Diary]
11 November 1930
I’m leaving the orphanage.

Clara’s here to look after things, and the children are quickly growing up.
I’ve done right and fulfilled my duty.

…Bloody hell! All the trouble started when that wretched child arrived…
I’ve done nothing to deserve this!
—

…That’s the end of the diary. We never saw Mr. Hoffman again.

[Martha's Letter]
24 November
Officer Dolittle,

My name is Martha Carol, and I work at the Rose Garden Orphanage. In the past
month, I have sent six letters to your attention, but have yet to receive a
response. Have my letters reached you? I ask that you please investigate this
matter at once for the safety of our children.

Yesterday, I saw them together again… Mr. Wilson and Wendy, a child at our
orphanage. I am very concerned for her safety. The two of them have been acting
quite strangely. Oh, it’s terribly odd… By strangely, I mean..

Mr. Wilson walking on all fours and nodding… and Wendy appears to be scolding
him… I don’t know how to explain it, except that it resembled dog training
gone wrong. Ooo… it gives me the shivers just thinking about it. Please come
investigate this matter as–

Also, January comes between October and November.

6 October From J to W
You’ve got it all wrong…

31 January From W to J
My dear Prince,
Yes, you are my Prince…

28 November From W to J
You still have that filthy dog?…

Also, the months you play through have NOTHING to do with documented months. Sir Peter wasn’t even supposed to be around until July when Brown was found, but gamescript bucketknight clues indicate the Sir Peter chapter was in May.