Kids finances and families are all different, but this worked for us.
Back in 2015 we got a call from our plebe; she was clearly upset, sad and angry. She just said “I really need to see you out here”. We jumped a Flt. from the West coast. By the time we got there DD was “all-good," (to this day I don’t know what prompted that visit request) . We were out there for a long weekend, DW and I took her into DC. She slept in a “real bed," went out to dinner, fell asleep watching PPV movies, shopped at Whole Foods. DD had fun, we had fun.
Started a pattern for us. DW and I traded off making solo trips to keep costs down and make logistics easier, but we got out there for visits in Oct, Feb, April every year DD was at USNA (made a science of it). Between visits to USNA and Holiday trips home DD got a break from the USNA Grind about every 8 weeks. Fast forward to DD’s 1C year, she was sitting at a desk at my
favorite hotel in Nap Town...
. DD looks up from her work and says: “Dad you have no Idea how much your visits helped me succeed here. About the time the grind of this place was getting to me and things felt dark, I’d look up at the calendar and I could start counting down the days until you or mom would be out here. Thank you”.
IMO the USNA is the best undergraduate school in the country, and an opportunity worth protecting for a DD/DS. In the OP's spot, unless my plebe is dead set on leaving, I tell him I want to help. I ask my him to make it just to Oct, and I will be out for the 3day weekend to take him into DC and unwind/do-the-town. As long as he hangs in, (and needs it), I’m giving him another “close target” to hit. People, families and finances differ but this really worked for our DD and I’d don’t regret the $$, vacation days, and other stuff we passed on to make those trips happen.
Note: They never call home when things are going great.