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We just went through this and switched from a Boulevard to a Radian RXT. Our Boulevard straps were always getting tangled and it was really hard for me to tighten enough (which was more than ClickTight thought). Now, it's super-easy to tighten by pulling the strap from behind the seat then using the front strap. Much better!

We also have a (forward-facing) Britax Frontier, and I find that easier to tighten than the Radian RXT.

I don't have any experience with the seat that you currently have, but we have the Graco 4Ever All in 1 and the Graco Extend 2 Fit for our son and both install very easily and are easy to adjust and tighten the straps on.

@LindsayInNY: I would get a combination seat for DD1 (a harness to booster seat) and worry about DD2 when a convertible is needed. New seats are always coming out so I would wait to see what best fits your needs then.

If you like the clicktight installation you could look at the britax frontier or pinnacle.
You may also like the chicco MyFit.

@LindsayInNY: They're fairly easy to clean, but not the easiest (like the Chicco Zip). If you and your husband are tall they do make a 4Ever version of the Extend to Fit. They didn't have it when I got my first one, but next baby will have one because husband and I are both 6'+.

@LindsayInNY: if you want the option of keeping your older one harnessed for longer, I’d probably do combination (harness to booster) now and get a new convertible when the baby needs it. My older daughter is 4.5 now and a number of her friends have moved to boosters. I know that my girl is definitely not mature enough for a high back booster yet, but it would be really hard to shell out a bunch of money on a combination seat knowing she would probably be in a booster within the year anyway.

We have a britax frontier harness to booster for her. She seems comfy and has a lot of room to grow, although she’s somewhat short. It’s very easy to install and tightening it or adjusting strap height is easy. But it’s very heavy and pretty wide- so we cannot fit a person in the middle seat between our two car seats. Our other seat is a nextfit which is also wide.

I agree on going combo. Your oldest can use until the younger needs it at which point older may be in a seatbelt booster. (Mine are 3 years apart and this is what we did ... older used from 3.5-6, then she was ready for booster (we put the combo in booster mode for a few weeks to try it, then switched it back) and younger got the combo which was helpful since he was about at the latch limit for his convertible and I didn’t want to deal with the seatbelt install). We have the frontier clicktight and I agree the straps are definitely easier than on britax convertibles. Clicktight was worth it to me since most kids that age are nearing the 40lb latch limit. It is kinda big and heavy but we rarely move it and it’s in a bucket seat.

Definitely a combination since she’s already FF. That way she keeps the seat until she’s ready to be out of a car seat/in a backless booster, and baby 2 gets his/her own convertible car seat until then. We really like the Britax Frontier, definitely preferred over the Graco seats DH and MIL have. The straps have never gotten twisted, and it’s easy to tighten. It was also really easy to install (I think that has more to do with the type of car though). I also like all the Diono seats and would choose that over the Britax. One thing I especially love about Dionos is the actual buckle itself: it’s sort of bulky, which makes it easier for preschoolers to buckle themselves. If you’re going for something a little lower priced I really like Evenflo and don’t hear those seats mentioned much here. My mom has convertible and combo Evenflos in her car and they’re super user friendly, easy to install (in anything but a Subaru), and the kids like them too.

@LindsayInNY: there have definitely been times when I wish we could comfortably seat a small adult. Like, I have squeezed back there in a pinch and can’t get both hips down at once. We have a mid size suv. Maybe look into a narrower combo seat- I think the Graco transitions is? My two seats are definitely on the wider side. We have two cars though so if we have visitors we just have to take both cars when we go somewhere.

We bought a Diono Radian RXT for my DD when she was just over 2 for RF and now FF. She should be able to use it for years to come yet (she is now 5.5) until she's outgrown the need for a high-back booster.
I love the fit, it's easy to install (the latch system has these quick-click and button-release functions) and both DH and I have done this ourselves and swapped this seat into his parents car before. It also folds up with backpack-type straps if you travel with it (we have not done this. Though that thing is pretty heavy, it is made of a steel frame so I appreciate that it's really solid. Also it's a narrow seat so I don't worry about fitting another infant seat in our cars come December.

We also just upgraded her seat in my DH's car which we use for school drop off and pickup. We wanted something more affordable since it's not the primary vehicle and went with an Evenflo Maestro. It can be used as FF with 5-point harness up to 50 lbs so we'll get some life out of that before it will be used as a belt-positioning high-back (110 lbs). It's not too wide (19 inches compared to the Diono 17 inches). Again, this should be the last seat of its kind we will buy for her. It's less than $80 on amazon so it's a LOT cheaper than the Radian. LO is comfortable in both seats.

I would not get a diono convertible for an already forward facing child unless you know for a fact you want to pass it down and use it rear facing soon. It does not make a usable booster for the vast majority of kids.