Hello TSK
Welcome to the wide world of model ship building. You are correct, plastic models of any subject are head and shoulders above kits from 15- 20 years ago. Add to that the variety of models(especially ships) available today and you have a great opportunity to get back into building quality models at an affordable price. There are many questions you have and many informational outlets availible to you. First and foremost is the internet, you'll never have to model as a "lone wolf". There are many ship model websites, just look 'em up, the wealth of info is amazing.
In the short term I'd suggest a sub model, or something similar, just to refresh yourself with the basics of modeling a ship. If you go with a surface ship, try an inexpensive model, go visit a well stocked hobby shop, and make a purchase, ask for advice from store personnel. As for painting...I have been modeling for a LONG tine and I stink at brush painting. Nothing enhances a model like a fine paint job but few modelers I know use brush painting. No airbrush, don't worry, there are a ton of "Rattle Can"(spray paint) colors availible to paint your model, many military colors to choose from. Tamiya offers the best quality spray paint on the market, it's a lacquer product, dries fast, and goes on like an airbrush. They are expensive however, and you should only spray outdoors or in a wide open area with good ventilation. For my money, a good air brush and a compressor are the way to go. The airbrush "system" is an investment, but worth it in the long run, I would guess most serious, long term builders own one(or two)!
Lastly FINE SCALE MODELER published a book (by reknown builder Mike Ashey) entitled "Building and Detailing Scale Model Ships". I believe it is still in print, the book contains many good tips on building any type of plastic and resin model ships.
Well, that's my two cents, good luck!
Mike M.