Your diagram of "tables" is not much help, but does indicate one problem. The vast majority of us can not easily reach 4 feet across a table. The usual recommendation is to limit reach to either 24 or 30 inches. Some will push that to 36 inches, depending on table height and actual length of reach.
For more help, provide a diagram of your entire area and show all obstructions (like the posts you identified in your first diagram) including windows, doors, mechanicals (HVAC, electric, water heater, etc.) and any areas you just can't use for a layout. Since it seems like you do this by hand, please use darker ink, try to print larger, and place all so that it can be read without having to turn the page upside down or on its side. Most of us look only at a computer screen and my neck just can't "crane" that easily any more.
Finally, give us some idea of what you want in a layout. From your first diagram, you seem to want an engine facility (including turntable) and the use of some industries. Does that mean you favor operations over loop running? Should loop running be given preference (and, if so, how many loops)? Have you looked for other track plans on this forum, or on other model railroad fora, and, if so, have you seen any you might like to adapt to your space?
With this info, members of this forum will be glad to help.
And, for the record, there is an Apple based track planning software called Railroad Modeler (I think) which might aid you in developing your own plans. There is also a completely free program called XtrakCAD which is downloadable and useable on Windows, Apple and Linux computers.
Chuck