First off sportster are not at the bottom. Its just a different type of bike for a different type of person (although I have a sportster and now find myself looking for a deluxe or road king). It all depends on what you want and type of riding.

However at 6'2" and 240lbs sportster will be to small.

I recommend the following
Fat Boy
Soft tail Deluxe
Road King.

 

+1 to this. I started riding again (after 20+ years of not riding) just a few months ago on an '02 Wide Glide. Best decision I ever made was buying a Harley. I rode some others (Shadows, Vulcans, and the like), and while they are nice bikes, there's nothing like a Harley.

Just take it slow, don't ride outside your skill level, and you'll be fine.

Good luck, ride safe, shiny side up....all that.

 

Good to educate yourself too, especially with a book like David Hough's "Proficient Motorcycling". There's all kinds of great advice with diagrams on what to watch out for. He's even has photos that make a point. One is of a regular street scene and you dismiss it at first until he points out that the car parked next to the curb has a clearly visible driver, and he's still inside! That's because cars that are pulled over may just pull out or even U-turn suddenly, right in front of you.

I came back after twenty years and the first two to three months were pretty paranoid until I learned more. The first year is statistically the biggie. And then after that you've survived long enough to know how to stay alive on the street. With all that said, you'll absolutely love the sport (if you like adventure!). I haven't had a boring motorcycle ride yet.

Other motorcycles are ok, dependable, etc, etc. But every Harley I've ever seen has some kind of presence, soul or whatever you want to call it. Hardly any are ever alike and no motorcycle sounds quite like a Harley, nor has the heritage and history behind it.

 

I think any Dyna would be good. Easy to throw around and low to the ground.

After riding a few at my local dealer, I swear that the Dyna feels like a piece of you when you ride...all natural movements.

 

my opinion, like many others, is avoid getting a sporty as a "starter bike." My friend just did so in April, is smaller than you, but he is already desperate to trade it on a Dyna. If you really must have a starter bike, I would go with your first thought and get a cheap metric cruiser, ride it like you stole it, then get your dream bike.

 

Nothing wrong with buying a cheap starter bike (read: metric). Buy a decent bike, but not too nice, ride it every day you can, and plan on trading it in next summer on the bike you're gonna keep for awhile. If you're first bike is too nice, you'll be less inclined to ride it on marginal days, and you need seat time. Put in about 6 or 7 thousand miles in a year, and you'll get a pretty good idea about what works and what doesn't work for you.

 

If he's going Harley don't even consider trading a metric. When I got my ultra, they appraised my vtx for trade. $3,000. Now, they'll take'em in on trade but they wholesale'em off. I sold it out right for $5,200 then made the deal.

 

Really you have two choices, play it safe and get a cheaper maybe used bike and make sure you really like riding and maybe give yourself some time to decide what you really want. The other is do some test rides and go for it, I have always believed in buying with your heart and not your head. Buy the one that makes you smile, it's a different bike for everyone. If it makes you smile you will ride.

 

Handling a 900 pound bike for the first time in traffic will scare the new rider right out of riding. Learning to ride the bike is secondary to learning to ride the bike in traffic and uncertain conditions.

 

Your almost too big for a sportster. Bike will look small.