The day I rode up Sugarloaf was on a ride with my Coast 2 Coast group. We started at the bike shop in Killarney and did 50 miles around the Clermont and Mineola area. The total elevation gain was 2,645 feet. I know the Horrible Hundred is done in that area but I would hate so see what the elevation gain is for the 100 mile route. That one ride was the most I had ever climbed in any bike ride I have done here in Florida. After doing this ride, I think I would rather do hills than get pounded by some of the consistent winds we have here. At least I can go down the hill and rest my legs some.

Yes, this area of Florida is extremely hilly; at least for us. It's about a 45-50 min drive north from my house to get to this area which is just west of Orlando. Obviously, our hills aren't as big or long as those out west or around the mountain states but it's what we have to work with. On this ride, I climbed 2,645 feet over 50 miles which would take me forever to do where I live. This morning's 51 mile ride yielded a total of 88 feet of elevation. :(

That great picture does not show a 3 mile climb, possibly half a mile to a mile at the very most!
Unless I don't understand what you wrote?
Yes hills are great fun to climb but not in intense heat, as we are experiencing these last few days!

First, the picture looks to be from a previous Horrible Hundred ride which is held in September.... Horrible Hundred 2016

Second, article about 2015 HH with 4,000+ feet of climbing....Horrible Hundred 2015 cycling routes available - Orlando Sentinel

Third, having biked the HH of 2015 and Six Gap of 2015, let me just mention that the 4,000+' of climbing during last year's HH was challenging and got me just as tuckered out as the 11,000+' of climbing during last year's Six Gap. Sugarloaf is strategically placed close to the end of the 100 miles so it is indeed a good workout.

Shifting gears like a real mountain biker
Often beginner mountain bikers use a pedaling speed which is too slow, say 55 – 60 revolutions per minute. This slow RPM or cadence puts unnecessary strain on your knees and kills your momentum at the hills. Slow pedaling also slows gear shifting by increasing the amount of time it takes for gear ramps and pins to help shift the chain.

Sure, we’re only talking the difference of seconds, but pedaling and hard produces shifting delays. And these delays ultimately affect the speed at which you think and act on the bike. So speed up that pedaling rhythm and not only will your gears shift faster, your confidence will improve and your decision-making on the bike will become faster too.

I run a 10 spd 12-30 with my compact 50-34, and get over most hills I see in Southern Cal. I have a Di2 Ultegra setup. Had a 28 rear originally. The change to 30 was noticable.

I'm one of those luddites that still runs a triple. On long climbs, I'm apt to put it in the granny and keep it there instead of using it as a bailout gar. I think my lowest gear is a 30/28.

I just had a knee replacement and was pretty worried about tackling the big mountain climbs here in my area- very hilly in the VA mountains. So I bought my new bike and had them customize it a bit to help take the stress off my new knee and old heart. It came with a Tiagra 50/34 compact crank- which I had them swap out for same 50/34- but in 165mm length.

They then put a 36 sprocket on my rear cassette. so I guess its 11/36 on the rear- or 12/36? Anyway- it works beautifully and gives me some serious granny gears. F and R derailleurs are still Tiagra that came stock.