A few of my solutions at the start of the series of solutions and the end of the row of solutions look the same colour as each other with the indicator. Shouldn't they be different?

That's a good observation. Universal Indicator is a mixture of indicators which shows a different colour for each pH number as far as this is possible. It is not as effective at giving distinct colours at either extremity of the range, as you have noticed.

When filling up my measuring cylinder, the meniscus was above the line and not right on it. Do I need to do it again?

No, don't worry if you have gone a tiny amount over the volume as this won't make much difference to the result. The solution is 10-fold more dilute than the previous solution.