The hardest thing about going cruising is not finding the right boat or making it fit your needs, no the hardest part is saying goodbye.
When you find your dreamboat and move aboard, you will be surrounded by other liveaboards in the marina. Liveaboards can be rather "interesting" people, but you will be too.
Getting a boat prepared will take time, and all the while you will be making friends with your fellow boating neighbors. It took me 5 years to transform an old blue water capable boat into a blue water cruiser. Over these 5 years I have made some very good friends. I would easily say that these friends are the best friends I have ever had, and that makes this the hardest part of all.
When you untie the lines, you will set off on your journey over the horizon. This also means that you will not see your friends anymore because you will be away.
We haven't untied the lines yet and we have already made plans to meet up with our friends in different places as we sail along, but visiting with them is very different from living near them.
Ben and Kate, one of our closest friends, live a few piers away from us. We will regularly just go knock on their hull unannounced, as do they, to go grab some food. Maddie works odd hours as a painting instructor, and Kate also works odd hours as a flight nurse. If either Ben or I are alone, we will go see what the other couple is up to and just hang out.
Once we are cruising though, we will give up this luxury. The only way we can meet up with them will be to schedule and plan ahead. This transforms the dynamic from spontaneous to planned.
This, in my opinion is the hardest thing about casting off to go cruising. While we are aware that we won't see them as regularly or as often, we are aware that we will come across many new people as we cruise, offering a glimmer of light in the darkness of the unknown that lays before us.