Easier? It really depends on the person and what they're trying to do.
What I find is that you spend a lot of money and effort doing the upgrade, which if you can get the small tank the way you like it, almost seems inevitable. Buying everything twice or three times as you upgrade is expensive (I know a lot of reefers who upgraded that many times in the first year or so, including myself).
A nano reef can also be just as expensive if you're going to go the more automated route, such as getting ATO, dosing/calcium reactors/controllers. Personally, if I'm going through that much trouble & expense, I'd rather do it on a bigger tank instead of a small "temporary" one that will get upgraded soon.
It also depends on whether its a fish only or reef. Small tanks have very limited bioload and it is very easy to exceed that carrying capacity and cause yourself headaches.
For a lot of people with limited space, an all-in-one (usually 14g to 34g) is a good solution.
For others who have more room, more $$ and time (and who are likely to get bit by the upgrade bug sooner rather than later), a larger tank is a better starting point. In a 4', my ideal tank has always been the 120g (4' x 2' x 2'). Max volume in min. space without getting your arm pits wet. I have known a few reefers who went the 55-75g to 90g to 120g upgrading route cause they only had 4' floor space available. So for me, if I can have only one tank and its a four-footer, I will go 120g. If its a 3' space, I would go 65g (3' x 18" x 2' tall). If my space is very limited, I'd get an all-in-one or cube.
As with everything else in this addiction, there are no definitive answers. Some people get into sw because they really want to keep tangs or large angels - so for them a 6' tank is needed and anything smaller is too small. I've known people who had terrible results with nanos but when they tried again with a bigger system, they had better luck. I've also known people who did great with a small system but couldn't seem to make the transition to a bigger tank when they upgraded.
The current (and past) nano reef contest is showing how there are many ways to do a nano (some will be KISS and others will be "break the bank" blinged out).
Getting an experienced reefer to mentor and help check out used systems can help get the best bang for the buck. IME, most reefers have a bit of OCD.
I am extremely OCD
This hobby can become extremely expensive very easily, which is why I never recommend people get into it. The first question I ask is "do you like having money in the bank?"
But if they are determined to make the jump into sw, then I am one of the believers in "the solution to pollution is dilution".
I also believe that it is more an art than a science.