I paid to have mine delivered since I was getting back into bikes, it was more than my ability with country roads, Interstate and sand/gravel from winter on all side roads.
It was well worth having my first ride not be my last.
How much money for a decent cruiser to start?
put the bike on 0% credit card through paypal, use www.leatherup.com for your gear cuz they have good deals there, take the lessons and your set...i have 6500$ bike on my credit card (I also make enough to pay it off relatively quickly before the 0% runs out) so just a thought