Many of the things you mention are true
to some extent, but there are a few "tricks" to it.
If you look like that picture, then you do indeed have a short frænulum - so-called Frænulum Breve, which is a sort of "medicalised" term which could convey an unfortunate implication that there was something wrong which required a "medical treatment" - such as surgery.
And indeed, surgery is commonly offered for it; for an adult such as yourself, this is
never a "hospital" procedure and would never require a general anaesthetic. I mention this as it would appear a number of men have been misled into accepting such an offer only to find that the surgeon had always intended to perform a circumcision instead on the absurd pretext that "when we got to it, it was the only way to fix it".
So much for the scary bit!
Firstly a clarification. In that picture, it is obvious that to cause the glans to bend down, considerable force is being applied to pull the foreskin tight (you can see the two fingers gripping it on the shaft). Either that, or the erection is not entirely firm, so that the glans is more mobile.
I have no doubt that pulling the foreskin back that firmly, and masturbating in such fashion (presumably using a "stroke" that alternately moves the foreskin over the glans and then pulls it right back) could be uncomfortable with a tight frænulum. The question is whether there is any
need to do so; clearly for masturbation it is only
one option and you are equally free to use a "stroke" which simply does not pull the foreskin back so vigorously
for the present.
But of course, you are worried about intercourse. There are two aspects here and you most wisely focus first on the use of a condom.
Well, I have to suspect that the information provided with condoms focuses on what one would call the "lowest common denominator" and in fact, manufacture (or ownership of the companies) may be in countries where circumcision is the more common.
The answer regarding application of the condom is that basically, you
put the condom on so that it covers all of the penis. There is some logic to pulling the foreskin back
as far as it readily goes where by "readily", I mean as far as is
comfortable.
Here's the trick: It's all about
lubrication - in fact,
sex is all about lubrication. You're a very lucky fellow, because you
have a foreskin, and a foreskin provides "automatic lubrication" for basic masturbation and to the extent that it works properly, for intercourse.
You know this bit about "pre-come" ("pre-cum") or pre-ejaculatory fluid? You may or may not have noticed it very much because my observation is that it actually takes a young lady's actual
presence to cause you to produce it to any substantial extent - Your Mileage May Vary.
Once you produce pre-ejaculatory fluid - as I suggest you will quite promptly when you are with your young lady (and do you actually have someone in mind at this stage?), then it won't
matter in the least
how you put the condom on, because your foreskin will move whichever way it chooses and the condom will slip freely over your foreskin and glans - wherever they are in relation to each other.
As a matter of fact, this becomes somewhat of a problem with condoms in general, for all men, because if this "slipperiness" extends all the way down to the base of the condom, the whole shebang moves
too easily over the penis and the only thing "holding" it in place, is the sort of "suction" at the end.
The big problem is that the young lady (may not always be young, but I'm posing this to your current age

) might not be quite "wet" enough on the outside of the condom, and the condom is preventing your pre-ejaculatory fluid from augmenting hers, and if she were to "grip" the condom tighter on the outside more firmly than you do on the inside, there is a marked tendency for the condom to slip off or be torn.
And looking forward to the prospect, one would hope of marriage where you are going to be having intercourse
without the condom, then either you have sufficient lubrication combining your pre-ejaculatory fluids, for your foreskin
not to be forcibly pulled back and risk pain and/ or tearing, or if there is not enough, then not only will
you risk these inconveniences, but risk causing
her substantial discomfort as well - not what you would want.
In short, whatever might be enough to hurt you by pulling back your foreskin, is equally to be avoided to ensure your partner's comfort, and is simply a sign that you were doing something
wrong.

And the practical part -
read through the previous threads here for further observations, individual experiences and so on. You need to identify where the attachment of the frænulum is to your foreskin so that you can grip this exact point and hold it stretched as in the picture Jim demonstrates -
this second picture illustrates that point somewhat better.