I don't know much, but here are some obervations from my experiences:
Seperate boat repair from cruising expences. You WILL have to repair the boat while cruising. Do some pretty serious vetting of the boat before leaving. Even then, prepare to repair the boat while underway. If leavin the USA, take spares.
Think of your lifestyle now. How much are you REALLY willing to change? How often to you go out to eat? What kind of food you eat? What do you do for entertainment? You get the idea....what do you spend now & what will change? Think this over before you answer too quickly. Take both of you into account.
Marinas. If you need to be tied to a dock (& shore power) you will find cruising a rather expensive activity. If you have the budget, all the power to you (no pun intended). We almost exclusively
anchor out. When we tie to a dock it's pretty much always a free dock (they are out there). I prefer anchoring out, but one should then become a student of anchoring and take it seriously. Just because the
anchor is overboard, does not mean you are anchored.
You will probably want to spent some time & money getting your boat outfitted to be more self-sufficient while you have a shore-side income (wind generator, solar power, water maker etc., etc.).
Glenn.
s/v Seawing.