1) People vary considerably in their willingness to trade off comfort/roominess for weight in a tent. I try to keep the weight under 3 lbs/person - so my solo tent is 2.5 lbs and my two-person tents are 4 lbs. and 5 lbs. respectively.

2) Freestanding tents normally still come with stakes and it's advisable to use them in case the wind picks up. But you can erect the tent just using the poles which makes it easy to move the tent around after it's put together if there's a tree root or rock in an inconvenient spot - or to shake out any dirt. And if you find that some of the stake positions can't be used due to rocky ground or sand that won't hold then it's not as critical as with a tent that depends on the stakes for support. OTOH, freestanding tents frequently require an extra pole compared to an equivalent tent that's not freestanding and that adds a bit of weight.

3) Both Hilleberg and REI make qood quality tents. Hilleberg concentrates more on designs that are suitable for mountain expeditions with the ability to sustain high snow loads and extremely high winds. Don't know about you, but if weather conditions get really bad on a bike tour I'll start looking for either indoor accommodations (hotel/motel, etc.) or a really sheltered spot for my tent. That's not an option when backpacking or mountaineering well above timberline. So there's a reason for having the design features of the Hilleberg tents, but they wouldn't be my first choice for bike touring. Providing that degree of strength and wind-proofing generally results in adding substantial cost, some extra weight, and reducing ventilation. I also agree with the recommendation to look at Big Agnes tents for bike touring.