Mikey, I dont know what your budget is on this one is but....
If I had to do it all over again, I would look at a 25-28 ft trailerable front cabin boat
Like a 27ft judge or big parker with dual steering stations and full canvas
Fuel efficient big 4stroke - 250-300 hp, sip gas on the troll- roll out at 40mph when needed
You can leave it in the slip for afterwork trips but still be mobile for Breezy, Solomons, PLO, CBBT, Del bay, Cape May, OC, NC, etc
Load it on the trailer and roll, small enough to handle yourself- big enough for 4-6 guys
Up front cost would be higher but you would have a lifetime rig
Very desirable rig as well if you ever had to unload it, good resale value
If I knew then what I know now.....
Good luck in your search bro
My 2cents