I did a lot of research on this at one point, and these are what I ended up going with and was quite pleased. You can probably find them cheaper at abe books or somewhere, I'm just linking amazon for the ease (hopefully amazon links are allowed)

https://www.amazon.com/Calculus-4th-Michael-Spivak/dp/091409...

https://www.amazon.com/Combined-Answer-Calculus-Fourth-Editi...

Spivak's Calculus - https://www.amazon.com/Calculus-4th-Michael-Spivak/dp/091409...

As always, it depends ...

If you just want to learn the maths relevant to your specific interests then you can simply pick a page on wikipedia, build a tree of topics you need to cover, then start to knock them off one by one, building a web of knowledge as you go. Then ask questions on http://math.stackexchange.com/ making sure you take the advice about how to ask questions the smart way[0][1].

If, on the other hand, you want to get into studying maths generally and build your maths study skills, then I would recommend starting with a really good maths text book and work through it, doing all the exercises, reviewing earlier material, and taking it seriously. Two options are Spivak[2][3] which claims to be about calculus, but is really about analysis, or "Sets and Groups" by Green[4]. The latter is great to create the underlying basic knowledge you need for cryptography, but more, it teaches you how to do maths properly.

You could also just pick something you think is interesting on Khan Academy[5] and go for it.

But having said all that, it's tough to get back into maths, and you need to make sure you really understand your motivation. Most people don't want to write a book, they want to have written a book. Most people don't want to study maths, they want to have studied maths. If you're not serious, you won't succeed, especially with no one to track your progress, answer questions, and generally encourage, coax, support, and inspire you, it will be tough.

How well motivated are you?

[0] http://www.catb.org/esr/faqs/smart-questions.html

[1] https://www.mikeash.com/getting_answers.html

[2] http://computo.fismat.umich.mx/~fhernandez/Cursos/Calculo201...

[3] http://www.amazon.com/Calculus-4th-Michael-Spivak/dp/0914098...

[4] https://www.amazon.co.uk/Sets-Groups-Course-Algebra-Second/d...

[5] https://www.khanacademy.org/

You can try "Data Science from Scratch" [0] to get some taste. It uses Python to teach essentials of data science, and ML altorithms. The code quality is very good, and there is an introduction to Statistics, Maths and Python to start.

Then you can continue with improving your maths (Linear Algebra [1], Calculus [2], [3]) and moving on with Statistical Learning [4] [5]. I am personally going now through this plan.

[0] http://shop.oreilly.com/product/0636920033400.do

[1] http://www.amazon.com/Linear-Algebra-Right-Undergraduate-Mat...

[2] http://www.amazon.com/Calculus-4th-Michael-Spivak/dp/0914098...

[3] http://www.amazon.com/Calculus-Manifolds-Approach-Classical-...

[4] http://www-bcf.usc.edu/~gareth/ISL/

[5] http://statweb.stanford.edu/~tibs/ElemStatLearn/

I agree. As far as calculus goes, I am more enamored with books like Spivak's (http://www.amazon.com/Calculus-4th-Michael-Spivak/dp/0914098...) that take a proof-centric approach to teach calculus from first principles.

Incidentally, for those who want to learn linear algebra for CS in a mooc setting there are 3 classes running at this very moment:

https://www.edx.org/course/linear-algebra-foundations-fronti... (from UT Austin)

https://www.edx.org/course/applications-linear-algebra-part-... (from Davidson)

http://coursera.org/course/matrix (from Brown)

The first 2 use matlab (and come with a free subscription to it for 6 months or so), the last python. One interesting part of the UT Austin class is that it teaches you an induction-tinged method for dealing with matrices that let you auto-generate code for manipulating them: http://edx-org-utaustinx.s3.amazonaws.com/UT501x/Spark/index... .

And of course there are Strang's lectures too, but those are sufficiently linked to elsewhere.

It's difficult to find what you are looking for, since maths is a much older field. However, Spivak's 'Calculus' is pretty close: http://www.amazon.com/gp/aw/d/0914098918.

What would be a good book series (preferably a classic one that's stood the test of time) on math (Algebra, various Calculus topics, Statistics, etc)?

I'd like to edit this some more during the edit window for this comment. To start, the books by Israel M. Gelfand, originally written for correspondence study.

http://gcpm.rutgers.edu/books.html

http://www.amazon.com/s?ie=UTF8&field-author=Israel%20M.%20G...

An acclaimed calculus book is Calculus by Michael Spivak.

http://www.amazon.com/Calculus-4th-Michael-Spivak/dp/0914098...

Also very good is the two-volume set by Tom Apostol.

http://www.amazon.com/Calculus-Vol-One-Variable-Introduction...

http://www.amazon.com/Calculus-Vol-Multi-Variable-Applicatio...

Those are all lovely, interesting books. A good bridge to mathematics beyond those is Vector Calculus, Linear Algebra, and Differential Forms: A Unified Approach by Hubbard and Hubbard.

http://matrixeditions.com/UnifiedApproach4th.html

A very good book series on more advanced mathematics is the Princeton University Press series by Elias Stein.

http://www.amazon.com/Fourier-Analysis-Introduction-Princeto...

Is this the kind of thing you are looking for? Maybe I can think of some more titles, and especially series, while I am still able to edit this comment.

   Anybody have insight into how to actualize these     nuggets into some semblance of a self-learning course? 

Buy Calculus by Micheal Spivak. Solve at least one problem every day. Make it ritual and a daily requirement. Watch MIT lectures for corresponding chapter you are on.

To learn this, don't trouble over the path and reason at present. Buy the book and start. Right now.

http://www.amazon.com/Calculus-4th-Michael-Spivak/dp/0914098...

Buy it. To learn this- buy it and start. Right now.

Get this book: http://matrixeditions.com/UnifiedApproach4th.html and work through it if you want a rigorous treatment of MV calc and intro analysis.

Or this book: http://www.amazon.com/gp/product/0914098918/ref=pd_lpo_k2_dp... for regular calculus. Read them, work through the problems, get an answer key, email your solutions to professors asking them to look at them.

You will get a good introduction to analysis (and exposure to many other parts of math) from those two books.

Spivak's Calculus, http://www.amazon.com/Calculus-4th-Michael-Spivak/dp/0914098... is a good bet. But it's very theory-involved.