The space is just one of those things you have to think about when choosing a town. When Late Night came out, people who have entered the HOF had to make lots all over the place to place them. Pam managed to get them all in over by Pinochle Point and probably still had some room for some of the new lot types around town. I understand there are more lots now but Metro & I have discussed it and decided that if we saw a picture of someone's town, we shouldn't have to look at the layout of the roads to know that they started in Sunset Valley. It's all a part of the strategy of the challenge to choose a town knowing the way it looks, the space it has for extra lots, the people in it. Putting the lots you know you have to have there for the plan you have going and knowing that you may not have every type that you want.
Remember if you have Pets - the Watering Hole Saloon is a smaller lot and is a dive bar just like Waylon's. If you have Supernatural, it requires a smaller lot for it's vampire lounge than the Plasma 501.
There is an entire section of Sunset Valley on Pinochle road that can have it's empty lots deleted and replaced with new ones for new lots. Put the junkyard next to the Bunches, throw the fire house next to the Frios and put the Salon next to Jamie Jolina. Now you have two 40 x 40 lots to place the eq center & Brightmore. The Grind sits comfortably next to Agnes and Mick's likes to sit right next door to that. If you have Katy Perry, you may have gotten the bonbon park placed, replace it with Performance Park so you can have a park stage for showtime careers. The town doesn't have to look pretty to be playable. Just as long as your Sims can get there, then it's not really much of a problem. Some of the LN bars have subway stations, on your first property put a subway station and then it doesn't matter if the bar is a little back from the road because you can just use the Subway to get there.
Does that make sense?