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I think some of the problem with fonts is they have "evolved" or maybe Devolved and there is apparently less uniformity. If THATS all your upset about as far as font's go you will probably fight that in almost all programs. Your background in typography may be a blessing and a curse. To tell the truth I usually make a rectangle box that is the exact height I want for a given font and then type on top of it and adjust until it's where I want it. If I think I will be doing MORE later as your project suggest I typically keep a working file with the various fonts styles and sizes over on one side and so the next time you can just grab the specific font for a specific spot on your sign and just retype the new words and save if off as a new cut file.

Cutter settings for different materials are determined by setting your blade depth, which is posted hundreds of times on here. Blade depth determines your force settings. Run your machine slow until you learn your machine. How to set your blade depth. To start with, you should set your blade depth correctly, by taking the blade holder out of the machine, and firmly cut across a piece of scrap vinyl, you will be cutting. You should only be cutting the vinyl and barely a mark on wax paper backing, Adjust blade to get there, Then put the blade holder back in machine, and use the force of the machine to get there, same results, only cutting the vinyl and barely a mark in wax paper backing. You should just barely see and feel the blade tip out of your blade holder. Vinyl is only a few mil thick, you only cut with the very tip of the blade. Use the TEST feature on your cutter. That is what it is for.

Lots of people use this logic but I never really understood it. If you have $10 cash in hand. Just put it in the bank, or a mason jar, and and don't touch it then spend $10 on your credit card. At the end of the month take the $10 out and pay the credit card. You're still spending the same amount of money. The only difference is you just keep track of what you spend vs what you make and don't spend more than you make. And if you get a good credit card you get cash back so using the credit card will actually save you money.

Do what you gotta do to make it work. Try to set some money aside from every job, so that you can eventually buy some vinyl.

Why contact paper rather than actual sign vinyl? 631 removable wall vinyl would be easy to apply to the wood and then remove and would not wear out your blade as quick.

Get Clean Cut Blades. They're wicked sharp and last a good long time, unless you abuse them.