I've got both a "sit up and beg" hybrid ( DS 8.4) and an Endurance geometry roadie (Avanti Cadent ERII 2) .
In terms of head wind, with a "sit up and beg" style bike you act like a sail and catch wind on your chest, so yeah the only thing you can try and do is make your frontal area smaller. Duck your head down a bit, wear tighter clothing...... Yes a roadie does help, you can get down on the drops and make yourself more aerodynamic.
For hills there's a number of factors. Of course hilly is a relative term. Here in Tassie is considered hilly by Australian standards. I live at 250m and a typical 1 hour ride for me will pickup between 450 and 800m elevation over about 25kms. But it's certainly not as "hilly" as some other countries
In terms of hills there's a number of factors:
1. Engine ( you can work on that one as you say )
2. Gearing - funnily enough having lots of lower gearing isn't necessarily better for hills. This is something I've considered lately after doing Mount Wellington , a 986m elevation gain over 31kms which I did on the DS ( complete divergence but I did it on the hybrid rather than the roadie cause I knew the bigger tires, extra weight and hydraulic brakes would make the down hill MUCH more fun
). While the gearing is a lot lower on the DS, climbs I do are often faster on the Roadie (34/28) than the DS (26/32). I think having lower gears just makes you "lazy" and you pick the lowest gear, pedal really quickly but not the most efficiently.
3. Weight - A lighter bike whether roadie or hybrid means less weight to "lug" up the hill.
Don't know if it helps but basically my experiences
In terms of the Escape, you're probably just not use to the different position and saddle though bruises isn't a good sign. By the sounds if you do go road bike you'd be best on an Endurance Geometry as it'll be less "bum up" generally than "
my neck was practically in a racing position" . That being said there's a lot of adjustment you can do to all these bikes to make the fit YOU correctly. Recommend you test ride a few other bikes both hybrid and roadie and see what works for you.
Just for fun here's a comparison of your Venture vs Giant Escape vs Giant Defy (Endurance) vs Giant TCR ("Race") . See how different the positions are (saddle to handlebar height difference, reach to bars etc) ? Sometimes you just don't notice how big the difference is when you just go and testride a bike.
