I can only help halfway. I don't fish, so I know nothing about that.
Retirement? Now 'ya talkin'. I can assist with that on many levels.
1.) It will grow on you. I was never the kind that got bored and needed a part-time job to keep from going nuts. I love having little to no commitments.
2.) Location-wise:
Anywhere South of the Mason/Dixon Line. Get away from cold weather.
I would avoid the Panhandle of Fla, LA, Miss or N. Texas. (Reference the 2020 Hurricane Season..it's almost Nov and Zeta is progged to hit on or around Louisiana Wed.)
We live on the Gulf Coast of Fla. We prefer it to the faster paced and busier East Coast. Plus, the Gulf is calmer on a regular basis than the Atlantic, allowing you more comfortable fishing days. (Knowing nothing about fishing, I don't know what's different to catch in the Atlantic than the Gulf. There are fish in both basins...)
Your Gulfstream will do well on the Gulf Coast. I had one for 10 years. Pick your days and be prepared for tight wind chop as opposed to the ocean swell off California. Anything over 2 footers is uncomfortable in a Gulfstream. In the summer months, the winds are light E SE & NE in the mornings followed by afternoon onshore sea breezes. The collision of the Gulf & Atlantic seabreeze boundaries create the afternoon & evening thunderstorms that Fla is famous for. Most of the summer months, the Gulf is relatively calm and inviting for offshore runs.
Then there's the winter....
The winds blow much stronger as cold fronts punch all the way thru to Cuba and bring days of NW to NE winds post-passage. There are good days, but much less frequent than in the summer months.
If you don't do 90- degrees and stifling humidity, re-consider Florida. We don't care, but others can't take it. Maybe the Carolinas??
These are great problems to have.. Luck to "Ya!