If you want a Harley then get a Harley. You won't regret it. You have taken the safety course already and you are already weighing your options. Sounds like you are ready to buy.
New bike or old bike does not change the way everyone else around you drives and that is the most dangerous part to riding on the road. I would lean towards the Heritage Classic personally but that is just me.
Good luck with whatever you decide.

 

Maybe you can somewhat answer your own question, being that you are older, wiser, more mature at this stage of the game.
IMHO, how you plan to use a motorcycle over the next few years should have zero consideration. Riding a motorcycle (well), having confidence, feeling comfortable, takes a bit of practice. It's a skill...a learned skill.


With that in mind, you must answer the question... what would be the best bike for me to really learn these skills on, given my present experience?
Good luck.

 

Start out with a cheap $500 UJM (GS650 in my case), get the fundamentals down regardless of how you feel about the bike. Once you got everything down to reflex level, then move on to a bike that you can get excited about. Too many before you and I have gone the route of thinking with your heart before your brain, and have paid for it with either their wallets or body parts.

 

OP-
This is only your first bike, not your last bike. Learn on a smaller/lighter/easier to handle tool, then move up in power/weight if you choose to.
If you must have a Harley, then get a Street 500. Ride it for a couple seasons, sell it for what you have got in it, then get your dream bike.

Studies have shown that learning to ride on a less intimidating motorcycle allows the rider to learn at a much quicker pace. How many years do you want to waste, learning how to ride? Lots, or as few as possible?

 

Go test ride the Fat Bob a couple more times to get comfortable with it or rent one for a day. Then buy it.

Oh - wait......don't buy it. Save up the extra money you need to buy the 114" version. Then buy that!

 

This 56 year old newbie's first bike is a 2017 Iron 883. Took the courses then practiced a lot. Got licensed in July and put on 1700 miles. The bike and I get along great.

 

[QUOTE=Prot;16919770]Your first bike shouldn't be a twenty thousand dollar eight hundred pound gorilla.

Most people recommend a used mid sized Japanese standard bike to get some experience on and to find out what you like and don't like. Something you can drop or crash without too much of a hit to your wallet.

Your body size and shape is a huge factor regardless and lacking that makes it impossible to make a good recommendation. Usually people start out with a used Honda Shadow VLX or something similar. It's an easy bike to learn and gain some experience on. They ride it for a year or two, sell it for nearly what they paid which wasn't much to begin with then buy what they really want. At that point, the smart thing to do is to rent a different bike each weekend. Consider this money as a good investment instead of making a twenty thousand dollar mistake.

(Agree with the above)
I was in this same position myself about ayear ago. Me, while I've ridden bikes here and there growing up, I've pretty much been an avid off roader the majority of my 50+years, so this was a bit different. Whatgot me on the street was I was given a Suzuki 200 dual sport bike as a resto-project bike.I ended up renovating it back to a nice 100% complete-clean bike, road it for awhile and really enjoyed it. So, that was what gave me the bug to look forsomething else. As both my brothers had street bikes, I decided to try it and so took the next step. Sold the Suzuki, added some add $ and picked up a 2005Honda VTX1300 twin with 7,900 miles for $3,800.00. Rode it for 7-8 months &put approx. 4K miles on it. I learned a lot of street skills, and developed abetter understanding of bikes traffic & other vehicles. My wife, while anti-motorcycle at first endedup warming up to it and going on rides. So, I decided to sell it and move up the chain. I ended up selling it for the same price Ipaid for it! So, with the wife warmed up to street riding I started researching Bikes & models. I ended up buying a new Road Glide. Ialso bought a 4 point docking station, tour pack, sissy bar and a 2ndbig squishy-wide seat. Those I put on whenshe goes, leave off when I go to keep a clean-sleeker bagger look.. lol.. Personally, I'd recommend a smaller older & cheaper bike to see if it's for you first before taking a $20K+ plunge.

 

Well.... spent a lot of time at my local H-D dealer again today. Rode more stuff. Today's adventures included a 2017 Slim S (the Army-green denim-finish one), another ride on the 2018 Bob (114), a 2018 Low Rider, and a used 2017 Fat Boy. I rode the Fat Boy twice about three hours apart. The second test ride was much longer than the first. I completely skipped test-riding the 2018 Fat Boy because of what I'd been reading about its 'steamroller' handling. I don't find that to be the case on the 2017. Very competent, predictable, manageable, and no unusual effort to maneuver it during normal road use. This particular one has louder-than-stock Vance and Hines pipes (which I noticed kept people around me more aware of my presence, as expected), ABS, cruise, stage 1 kit on the engine (which I didn't find made the 103 engine in any way too much to handle; I thought the stock 110 on the Slim S that I rode felt a bit twitchier by comparison). I'm a bit surprised that the wet weight of this bike is 730 lbs; it didn't feel tremendously heavy to me during the ride (I did not, of course, have to pick it up off the ground). Only 1,400 miles on it; the previous owner apparently traded it in on an anniversary-edition Road Glide. Asking price is about $3K less than the base MSRP of a new 2018. Blue/silver paint.

Not rushing through this, but this one seems like a solid deal considering the care, add-ons, and my comfort with it so far.

 

Seems like you are a very rational person stuck in an emotional decision. Yep, buying a bike is always emotional like you said or why even bother buying one.... If you like the used Fat Boy research the value of the used bike. Including the salvage value. Depending on the dealers business model they may get rid of the bike to an auction house for salvage value to keep inventory turning over. Find out how long the bike has been on the floor. At least shoot for the lowest retail number you can find and get some goodies or service thrown in. Would be a good deal. Note the upgrades like the V&H pipes are worthless for used pricing. No one gives you money for upgrades but they will tell you hey this bike has $600 slip-on's already installed, so what.... they did not give the previous owner $600 for them. Also please test ride the 2018 Fat Boy, was told it handles great (I have not ridden one). Was told the sales folks all loved the bike because it was so stable. Good luck, please post pics!!