Unfortunately, the 25+ situation is common in the Chassidishe crowd as well. The bottom denominator is very often money. The Rosh Yeshiva in our group whose daughter just got engaged at 23 B”H, when asked what the story was, we were told that most boys want at least support of $1,000 a month to which he replied he does not have and won’t lie, when a shaddchan suggested that he lie and after 2 months say he can’t. I know of 26+ girls who already own a house(no mortgage) and earn enough to support a family but many boys(actually it is usually the parent(s)) want the support to come from the parents!
About girls marrying widowers, it is happening in all circles. These girls are very special as the ones that i know who did it are doing a great job. The most recent is a shidduch of a 26 year old engaged to her brother in law, a widower of her sister A”H. Who are we to understand the ways of Hashem!?!?!?!?