I would say that when I speak, I pronounce we will as 'wheel'. Like a car wheel or by cycle wheel. With the sentence read it with, I would say the it and wth are pronounced separate, it's the first two that I would join. I would pronounce that sentence like this 'Reddit with' . Hope this helps!

Well, if you're familiar with IPA transcriptions, I'd suggest pronouncing "we will" together, so you should end up with something like /wiwl̩/ or /wɪwl̩/ As for "read it with", there are two ways of doing this; one is to pronounce the /t/ in "it" and the /d/ in "read" as glottal stops /ʔ/. Since "read" already has a long /iː/, it would be relatively easy to pull off, and you should end up with something like /riːʔ ͜ ɪʔ wɪð/. However, I wouldn't recommend doing this if you speak American English. It's a very British thing to do. In that case, you can use the American "t" in "butter" (/ɾ/) for both sounds, and make the second /ɾ/ sound less voiced (almost as if it wasn't there at all) While these may not be the best solutions, they are very good "hacks" I suppose Hope this helped in any way!