Welcome AgentZ, I'm new here and afraid I've developed a slight "forum addiction"... I can quit anytime I want to, really I can... Good folks here w/ good advise.
As far as which bike to buy, I was in the same predictament about a year ago. Knew I wanted a Harley, but didn't want to drop my hard earnerd cash and find out I bought the "wrong" model a month later.
What I did was to go to the local dealer in Las Vegas and rent a different model about once a month. Rode a Fatboy, Ultra Classic, Electra Glide Standard, Road Glide, Springer Softail and finaly settled on a Road Glide.
$100 for a rental for 24 hours bought be peace of mind that I got what I wanted. Started watching ebay, Cycle Trader as well as the local paper for a used TC88 Road Glide and finally found a 1999 in Seattle. Made the deal and bought it sight unseem after many phone calls and emails.
Think I got a good deal and the HD I wanted.
Also, I got to ride the rentals for over a year and had a bunch of fun until I found my bike...
Good Luck and let me know what you settle on!