Designers - What's Your Take On Remaking Commercial Fonts?

I’m a budding design freelancer and have been wondering about the issue with font useage: in particular, commercial fonts that cost far too much to be able to afford at this point, being in the startup phase of a business.

Now, I’m NOT asking for opinions about stealing or illegit use.

I’m only curious about certain aspects that might (or might not?) be considered OK to do, in your opinions.

Let’s say I’m going for a headline of a magazine, website banner, a logotype or something therealikes:

Acquiring (about which we don’t need to go into further detail) some commercial fonts which has the attributes of what you’re looking for; and from a chosen font, redesigning the letters into something new enough, to safely being able to consider it new to the original. (<- if yes to this, here’s an interesting sub-point of thought, then: even though you’ve reworked original beyond a degree of perceptible duplication, or even more than so; would you hesitate doing something that you can ultimately call ‘your own’, yet, still it’s pretty obvious that it reminds of the original font?)

Furthermore, (I’d appreciate your honesty) would you get hold of all kinds of font libraries from the spooky underwebs, and do like the above example, or would you rather just sit there, with a near-zero budget, without any fonts, and (if this is the case) feeling less motivated designing your own font sets, since you really don’t have time for that right now? I can sense, there’s a third approach to this, which, of course, would be to take a look at the great font foundries’ websites and make your own variations, inspired by what you like, which is (still) something that might touch upon what I asked in the former paragraph above…

A few last notes to this question

Note 1: I am aware of some few more or less cheap libraries, but in the end, those just might not be enough.

Note 2: I’m a poor startup. Very, very poor.

Note 3: my question doesn’t relate to situations where I’m commissioned by a client, in which case I could just point the client to a suggested typeface, and perhaps arrange for a deal where the client buys the font and I supply the design. I’m more thinking about scenarios such as design contests, proposals, stock design and likewise.

Note 4: I don’t know if this is a taboo question or not, or if it sounds non-serious, but this has been a pressing question for me, for some time now.