what kind of environment do you live in? Urban? Suburban? Rural? What kinds of activities do you do a lot of? Do you go to malls? Do you walk around city streets and parks? graveled nature paths? do you travel a lot (by car) to other destinations (beaches, cities, etc)? do you (or DH) jog?
i think whether or not you will get use out of a stroller has a lot to do with your surroundings and your lifestyle. when i had DD1, i lived in the middle of a large city. i wore her everywhere, but had a light umbrella-style stroller (a Chicco) that carried our diaper bag and changes of clothes and a few toys and a snack, and sometimes the groceries on the way home from the park. occasionally it even carried DD1

i also watched another little girl two days a week, so i often wore one and pushed one. we used it every single day and it was an indispensable piece of baby gear.
but now we live in a rural area, there are no sidewalks and no 'town' to speak of. we're not mall-goers or shoppers in general, except at places we need to go for necessities like the grocery store and there i just use a cart if i don't want to babywear. it has been sitting in our barn collecting dust for almost 3 years. it got used once - when we went back to our old neighborhood to stay with friends for a weekend, and one of our older two would occasionally ride in it when they got tired of walking, and it carried some gear for us which was nice.
i do have a bicycle trailer that coverts to a stroller and we do still get some use out of that because it can go "off-road" on gravelled nature paths an things, and it seats two (which is nice when you have 3 kids). but if that were the only kind of environment you might use a stroller, you'd have to decide if it was worth buying something beefier. an umbrella stroller there would be useless, though they work just great on flat paved surfaces. or if you or your DH do a lot of jogging, a jogging stroller would be idea.
so i think you need to think about how/why/where you might use a stroller to see if would be worth buying one, and what kind of stroller would be of best use.