Kcinnick,
I hope you are not feeling too beat up, but all have had some good advice, probably the best is to work in a sign shop for 3 months (a year is far better, but not easy to do).
Adding a few thoughts here for you from what we have learned. We are a full time operation and have been from day one, we have 1 FT employee usually and a part timer during the summer. We are not a franchise, but part of a large group of sign companies that has a number of bennifits being in a large group. We invested far more that was planned and while the original plan was to have employees do all the work, that has not proved to be viable for us.
Signs and garments are very cut throat, and the customer base will work you hard, we started our sign business 6 years ago after operating two other completly different businesses (some of us are just not too bright
You will need more than a couple of books to get you going, the equipment sellers all tell you how easy it is to make a profit and sell the items (ha). To be able to make money you will need to do a multiple of things until such time as you can specialize, and that will depend on your area. At this point in our business we do banners, flat signs, wraps, vinyl installs (when I cannot get out of installs) as well a laser engraved signs, tags and we do T shirts with a Brother T shirt DTG 541 printer. We have invested a lot of money in equipment and supplies to be where we are now, and it has been an expensive learning curve.
You will need good software to support your efforts depending what you are doing,
we have Corel Draw, Illistrator, Photoshop, Flexi, and add ons for them. On any given day we are using them all as no one has everything in it I want. Most of our design work is done is Flexi. You will also at some point need software for generating quotes but to begin with there are several excellent resources out there, again no one will be the end all to be all, just too many variables in making a sign.
You will need to invest in inventory and depending on who is close to you will determine the amount of inventory you need to carry, as customers will not want to wait very long once they OK a proof-.
As for screen printing, my friend/competitor who does it only makes money on large school orders, works lots of hours as everything is a rush, and shop stinks bad and has lots of waste because he is constantly getting new help.
Something else that is very important is the sales and marketing efforts, if you are working during the daytime how will you contact new clients? and equally if not more so important, how will they get ahold of you? They call, no answer, move on to the next on the list!
Take a good look at the competition in your area, small shops, big shops, out of the home, franchised ect. Do some research you may get your eye's opened.
As for some easier items to do, a garment printer is not a bad way to go, but at 20K you need to do some serious shirts every month AND I can't say for other brands but the Brother G541 you need to do a least a clean cycle every day (can take an occassional weekend off) or it will clog the heads (Brother salesmen say it doesn't require daily or even weekly cleans----but they are trying to sell it)
A laser engraver can be profitable if you can find a client base for it 16-20K new, very little maintence, if doing gift items will need to hook up with a gift shop.
Digital printer, can print banners/signs, can have signifigant investment in inventory to feed it with differend medias, and repairs can be extremely costly.
Wow, didn't mean to make such a long post! Not to discourge you, but have your eyes wide open, we enjoy our shop, but it is a lot of work and not near as profitable as we think it should be. Best of luck to you in what ever direction you go!
Hal