This prototype answers the main question(s) and the minor question. It will capture each line of a paragraph, one at the time, and loads them into tikz
nodes.
The capture is done using
Werner's command which uses \lastbox
.
The command \TypesetLines{<text>}
will display the lines using the x and y offsets, and an optional rotation, using the commands generated by
\RotateAndGo[<optional rotation angle>]{<consecutive number id>}{<x offset from corner>}{<y offset from corner>}
There are two modes of operation:
(1) With the manual mode you choose the rotation and position of each line with a \RotateAndGo
per line.
The number of \RotateAndGo
required is at least equal as the number of lines.
(2) In automatic mode
the parameters needed for \RotateAndGo
are dynamically generated based on the number id
(or other variable) by including its execution in the \makenodes
command.
Each line is added to the tikz
node together with a tikzmark
with the same number id
as the line.
This allows an arrow to be drawn from anywhere on the page to the baseline at the beginning of any line.

Manual mode

Automatic mode: the starting points of the lines follow a quadratic curve.

\documentclass{article}
\usepackage{tikz}
\usetikzlibrary{tikzmark} % needed <<<<<<<<<<
\usepackage[showframe]{geometry}
\newsavebox{\singleline}
\newcounter{xcount}\setcounter{xcount}{0}
\newcounter{xlinecount}
% From https://tex.stackexchange.com/a/57140/161015
\newcommand{\getlines}{% capture all lines of a paragraph and puts them in their place
\setbox\singleline\lastbox%
\ifvoid\singleline%
\noindent\ignorespaces%
\else
\unskip\unpenalty%
\begingroup\getlines\endgroup
\stepcounter{xcount}\setcounter{xlinecount}{\value{xcount}}\par
\makenodes
\fi}
\newcommand{\makenodes}{}
\newcommand{\TypesetLines}[1]{\parindent0pt\vbox{#1\par\getlines}} % load the paragraph and display the lines
%\RotateAndGo[<optional rotation angle>]{<number ID >}{<x shift from corner>}{<y shift from corner>}
\newcommand{\RotateAndGo}[4][0]{% save rotation and shifts
\expandafter\expandafter\expandafter\newcommand \csname R#2\endcsname{#1}%
\expandafter\expandafter\expandafter\newcommand \csname Cx#2\endcsname{#3}%
\expandafter\expandafter\expandafter\newcommand \csname Cy#2\endcsname{#4}%
}
\begin{document}
\pagestyle{empty}
% First example ********************************************
\newgeometry{textwidth=4.0cm}
\renewcommand{\makenodes}{%put the lines in their place, automatic mode
\RotateAndGo{\thexcount}{1cm}{-0.5in*\thexcount} % only y-shift
\tikz\node[inner sep=0pt,rotate=\expandafter\csname R\thexcount\endcsname, remember picture, overlay, anchor= west ,draw]
at ([xshift=\expandafter\csname Cx\thexcount\endcsname, yshift=\expandafter\csname Cy\thexcount\endcsname] current page.south west)
{\tikzmark{\thexcount}\usebox{\singleline}}; % typeset
}
\noindent Some text spanning three lines with very nice automatic line breaks \bigskip
From \tikzmarknode{here}~HERE to the first line baseline
\TypesetLines{Some text spanning three lines with very nice automatic line breaks}
\tikz[remember picture,overlay] \draw[->,red, very thick] (here) -- (pic cs:1); % the arrow to the baseline of the first line (# 1)
\newpage
% Second example ********************************************
\newgeometry{textwidth=4in}
\renewcommand{\makenodes}{%put the lines in their place, manual mode <<<<<<<<<<<<<<<<<<<<
\tikz\node[inner sep=0pt,rotate=\expandafter\csname R\thexcount\endcsname, remember picture, overlay, anchor= west ,draw]
at ([xshift=\expandafter\csname Cx\thexcount\endcsname, yshift=\expandafter\csname Cy\thexcount\endcsname] current page.south west)
{\tikzmark{\thexcount}\usebox{\singleline}}; % typeset
}
\noindent As any dedicated reader can clearly see, the Ideal of
practical reason is a representation of, as far as I know, the things
in themselves; as I have shown elsewhere, the phenomena should only be
used as a canon for our understanding.The paralogisms of practical
reason are what first give rise to the architectonic of practical
reason.
\bigskip
Arrow to the \tikzmarknode{last}~LAST line (\# \verb|\thexlinecount|)
Last used line= \thexlinecount
\newcounter{ctrx}\setcounter{ctrx}{\value{xlinecount}}
\addtocounter{ctrx}{1}
\RotateAndGo[0]{\thectrx}{0in}{-1in} % first line here is # 4
\addtocounter{ctrx}{1}
\RotateAndGo[-90]{\thectrx}{0in}{-1in}
\addtocounter{ctrx}{1}
\RotateAndGo[-90]{\thectrx}{2in}{-1in+\baselineskip}
\addtocounter{ctrx}{1}
\RotateAndGo[-90]{\thectrx}{4in}{-1in+2\baselineskip}
\addtocounter{ctrx}{1}
\RotateAndGo{\thectrx}{0.in}{-4.7in}
\TypesetLines{As any dedicated reader can clearly see, the Ideal of
practical reason is a representation of, as far as I know, the things
in themselves; as I have shown elsewhere, the phenomena should only be
used as a canon for our understanding.The paralogisms of practical
reason are what first give rise to the architectonic of practical
reason.}
\tikz[remember picture,overlay] \draw[->,red, very thick] (last) -- (pic cs:\thexlinecount); % the arrow to the baseline of the last line
\newpage
% Third example********************************************
\newgeometry{textwidth=3in,showframe=false}
\renewcommand{\makenodes}{%put the lines in their place
\RotateAndGo{\thexcount}{-10pt*(\thexcount-9)*(\thexcount-9)+4in}{-1ex*\thexcount-1in} %changed <<<<<
\tikz\node[blue, inner sep=0pt,rotate=\expandafter\csname R\thexcount\endcsname, remember picture, overlay] %changed <<<<<
at ([xshift=\expandafter\csname Cx\thexcount\endcsname, yshift=\expandafter\csname Cy\thexcount\endcsname] current page.south west)
{\tikzmark{\thexcount}\usebox{\singleline}}; % typeset
}
\TypesetLines{\raggedright As any dedicated reader can clearly see, the Ideal of
practical reason is a representation of, as far as I know, the things
in themselves; as I have shown elsewhere, the phenomena should only be
used as a canon for our understanding.The paralogisms of practical
reason are what first give rise to the architectonic of practical
reason.}
\end{document}
This is a "light" version, to be used only in automatic mode (that is, without prior individual assignments to each line).
\documentclass{article}
\usepackage{tikz}
\usetikzlibrary{tikzmark} % needed <<<<<<<<<<
\usepackage{calc}% needed <<<<<<<<<<
\usepackage[showframe]{geometry}
\newsavebox{\singleline}
\newcounter{xcount}\setcounter{xcount}{0}
\newcounter{xlinecount}
% From https://tex.stackexchange.com/a/57140/161015
\newcommand{\getlines}{% capture all lines of a paragraph and puts them in their place
\setbox\singleline\lastbox%
\ifvoid\singleline%
\noindent\ignorespaces%
\else
\unskip\unpenalty%
\begingroup\getlines\endgroup
\stepcounter{xcount}\setcounter{xlinecount}{\value{xcount}}\par
\makenodes
\fi}
\newcommand{\makenodes}{}
\newcommand{\TypesetLines}[1]{\parindent0pt\vbox{#1\par\getlines}} % load the paragraph and display the lines
\newcounter{anglex} \newlength{\Cx}\newlength{\Cy}
\newcommand{\RotateAndGo}[3][0]{% save rotation and shifts changed <<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<<
\setcounter{anglex}{#1}\setlength{\Cx}{#2}\setlength{\Cy}{#3}
}
\begin{document}
\pagestyle{empty}
% First example ********************************************
\newgeometry{textwidth=4.0cm}
\renewcommand{\makenodes}{%put the lines in their place, automatic mode
\RotateAndGo{1cm}{-0.5in*\thexcount} % only y-shift
\tikz\node[inner sep=0pt,rotate=\theanglex, remember picture, overlay, anchor= west ,draw]
at ([xshift=\the\Cx, yshift=\the\Cy] current page.south west)
{\tikzmark{\thexcount}\usebox{\singleline}}; % typeset
}
\noindent Some text spanning three lines with very nice automatic line breaks \bigskip
From \tikzmarknode{here}~HERE to the first line baseline
\TypesetLines{Some text spanning three lines with very nice automatic line breaks}
\tikz[remember picture,overlay] \draw[->,red, very thick] (here) -- (pic cs:1); % the arrow to the baseline of the first line (# 1)
\newpage
% Fourth example ********************************************
\newgeometry{textwidth=2in,showframe=false}
\renewcommand{\makenodes}{%put the lines in their place
\RotateAndGo{-10pt*(\thexcount-9)*(\thexcount-9)+3in}{-1ex*\thexcount-1in} %changed <<<<<
\tikz\node[blue, inner sep=0pt,rotate=\theanglex, remember picture, overlay] %changed <<<<<
at ([xshift=\the\Cx, yshift=\the\Cy] current page.south west)
{\tikzmark{\thexcount}\usebox{\singleline}}; % typeset
}
\TypesetLines{\raggedright As any dedicated reader can clearly see, the Ideal of
practical reason is a representation of, as far as I know, the things
in themselves; as I have shown elsewhere, the phenomena should only be
used as a canon for our understanding.The paralogisms of practical
reason are what first give rise to the architectonic of practical
reason.}
\end{document}

% at this point insert code to put the box at the correct position
(which will probably be hard for you regardless)?