(I'm very new to diesel maintenance so please excuse my rookie mistakes here!)

My MD11C has been cutting out on me more and more frequently in a way that made it sound fuel starved. Each time it would restart immediately... the theory was that it was picking up contaminants in the fuel and when the pressure cleared those backed out. I put it on the low priority list to fix, figuring that I'd eventually polish the fuel. Haha.
So now it's cutting out enough I've moved it up to the "very high priority."

I'm starting with the fuel filter. I have the original giant black fuel filter bolted to the side of the engine compartment. It's likely 1978. I undid the bottom screw and out poured 1/4 gallon of very black fuel. I have no idea when the PO last did that. I tried to undo the top of the filter but it appears wedged or rusted.
So now I want to replace that "Specialty Marine" filter with a Racor 225 filter. The first problem I've run in to is that the fuel hoses coming from the fuel tank are metal tubes screwed in to the fiberglass and, of course, don't line up with the holes on the Racor.
So my questions are:
1. Can I buy flexible hoses to connect from the original hoses to points that match the Racor?
2. Any gotchas that any one would like to point out with this entire project? I hopefully learned early enough that you need to close the seawater intake if you're going to be cranking a lot.
3. I've seen some threads on bleeding after fuel filter change... I hope I get that right.
4. Is there any chance that the dirt in the only fuel filter could have made it through in to the next part of the fuel system? Any suggestions how I would check?
5. Anyone recommend a mobile diesel mechanic willing to come to SF in case I can't manage to get this done?
Attached are some pics of the engine and the old fuel filter.
Thanks in advance for any advice that you can take the time to offer!
John Speck
Pearson 323
Lucky Mud
Hull #110