Is it all worth it?

Mid-Fi is about the best you can say regarding Boston speakers.  Look at the construction and specs of the A40, truly awful. This is not a high quality speaker, and it cannot produce upper end sound relative to others. Yeah, you save a lot of money, but you do not somehow leapfrog the performance of better speakers. You only get what you can achieve with any speaker, a relative improvement limited by the speaker. Put a better speaker in the rig and the differences would become apparent. 

Further, you might prefer a better speaker and affordable electronics to the pricey stuff and A40. Only listening would tell. i.e. If you spent $10K on electronics and use the A40, you may prefer a receiver with a lower price Magenpan and come out far ahead in terms of cost. So, no the A40 doesn't make me think much of it.  :) 

Mapman, well, let's have your list. When you say, "...compete with new stuff citing many times more somewhat surprisingly," let's hear the names and models of speakers these nearly free speakers compete well against. To what have you compared them directly to draw that conclusion? 

I own a pair of somewhat newer Boston Acoustics bookshelf speakers with the same construction and 6" bass and 3/4" tweeter. I got them for $10 at a garage sale, and I use them in my� garage system. 

I compared them directly (blind comparison, even) when I wrote the Audio by Van Alstine ABX Comparator article and pitted them against the Insignia 6" coaxial two-way speakers which were initially $50/pr. So, I had both of these in my main rig for that purpose.  I also have a pair of older Paradigm Micro speakers, which has more refined sound quality than these others. What speakers you have in mind that are "many times more" that the A40 beats? 

I can think of a situation in which some tiny bookshelf speakers with 3" bass drivers might sound "worse" to some ears than the A40, simply because the A40 would go deeper in the bass. 

My salvation came in the form of variety. When a person is endlessly pursuing "the One," it's a good clue that they won't find it. Very likely there is an insatiable drive to hear something different, no matter how good the rig. Buying and dumping won't address the need. The need is to enjoy the variety and gear as much as the music, and there is nothing wrong with that. It's a fabulous way to enjoy the hobby. 

The solution is simple; divvy up the budget to get the best components or speakers to express variety, and watch how satisfaction blossoms. Bored? Simply change some cables, a component or speakers. If one has the space and the means but is not willing to spend the money on this, then there is no justification for complaint, especially when at all price levels this diversification can happen, even with inexpensive speakers such as the A40. 

For instance, something as simple as having a pair of more affordable panel speakers on hand to swap out with the main speakers can keep much of the OCD-like dissatisfaction away.  Or, if on a severely restricted budget, find several garage sale or thrift store speakers and rotate them. The variety of experience is lovely, and it doesn't need to be costly.