1) Does NOT require big $$$ to get into astronomy. I would suggest a 6 or 8 inch dobsonian reflector as great starters. Either can be had for well under 500. These type scopes are max values because all the money is in the optics, not fancy computerized mounts, bells and whistles. A good place to start is www.telescope.com which is Orion scopes. I have a 10" dob from them and is a great scope. i use to have a 16" meade dob, but thats another story 😆
2) Would love to give you a sky tour, give you hands on experience on the journey. Since you are in the keys, u should chk out the "winter star party" , huge gathering of amateurs in lower keys. Be glad to answer any ? you might have..