The easiest way to look at a condition that has multiple parts, is to look at each part separately.

Since the question is about the #1A specifically, let's pay attention to that horse.
Has this horse EVER won a race "OTHER THAN"....
1 - a maiden race?
2 - a claiming race?
3 - a starter race?
4 - a PA Bred race?
The answer is "NO"
It's first win was vs. maidens...OK
It's next (2) wins were vs. claimers...OK
it's 4th win was vs. SA(starter)...OK
So this horse QUALIFIES for this race.
Now, for any other horses, who may not fit this condition as well as the #1A, there is an additional condition...
OR, "which have never won 2 races".
Why is that there?
As an example, let's say for some unknown reason, a horse is entered in a small stake race in its' first lifetime start and WINS IT!!
In this case, it would not qualify on the first part of the condition because it was "OTHER THAN" a maiden, claiming, starter or PA Bred race. It was a Stake race.
However, it has not won (2) lifetime races, so it is still eligible for this condition.
About the "allowances".

Take note at the end of the condition, the very next word is "Weight". Then it explains. If a horse hasn't won a race since December 1, 2012, it gets 3 lbs. off. If a horse hasn't won a race since November 1, 2012, it gets 5 lbs. off.
Finally, it stipulates that wins in a claiming race are not considered in the allowances for weight. In other words, if the horses wins were in claiming races it DOES NOT get any weight off.
If the horse won a race in one of the other types of qualifying races and it won such as race since December 1 2012, it DOES NOT get any weight off.
So let's take a look at the #1A horse.
1 - first win was a Maiden CLAIMER...no weight off
2 - the next (2) wins were in CLAIMING races, so again, there is no weight off
3 - its' 4th win was in a STARTER race, but that was on December 9th, 2012, so again, it gets no weight off.
How can we be sure?
In the conditions, right next to the word "Weight", it says 122 lbs.
Now let's look at the entries.