Hey Luke... I see so much similarity in our threads. I too have been looking at bigger boats. My problem is no one around me family wise is interested. The whole idea for me was a trailer sailer that I could take out, rig, launch, days sail or weekend camp, haul out, de-rig, tow away and pack away for the next few months till the sailing day or urge comes up. Mooring fee's at my local club are the most expensive in South Africa... the main point to not wanting to keep a boat on a mooring. A swing mooring is cheaper however the boat becomes a sea bird sanctuary with the lovely coating of guano that is oh so appealing... or it's a target for the myriad of thieving scavengers loitering around the suburbs these days.
Priorities change over time, just like desires. What works for you today may not work for you in the future. Family, personal health and financial security is what it boils down too. Applause for starting your own business. I ended up in hospital for working my self to death chasing money... no one thanked me for spending endless days at work - No One!
Anyways... like you I have spent way to much money and time on the boat to just sell it without at least sailing it for a season. There is also no ways I would recoupe what I got in it... new or otherwise. Unless you buy a brand spanking new boat that is genuinely "turn key" ready you just going to buy a bigger project boat.
As they say though "whatever floats your boat"! All the best for you and yours in your decision making process.