So just a quick comment on the one day trip.
It wasn't bad at all. Makes for a long day, but I was up at 4:40am----flight out at 6:50---landed around 9am local west coast----we went and ate and still had about an hour and a half to burn before gates opened----got in around 11:40am to stadium----game----left about 3:30 and were able to go to some really cool breweries on old Alameda Navy Base from 4-5pm or so-----uber back to Oakland Airport and got through and to the gate right around 5:50pm for start of boarding and flight took off at 6:20pm. Landed right after midnight central time.
Didn't feel rushed at all really at any time during the day. Long flight to Oakland, so if this was being done in say St Louis or KC or something it would be even easier.
I would recommend if you don't care to really stay in the town you are going to, or have no desire to sightsee etc. I have already looked at flight times and potentially will do this again for my trip to Citi Field because I still need it as one of the 9 stadiums I have not been to, but I fucking have no desire to stay in NYC. I have been there twice in my life already and have done the whole tourist shit, so I am over that place. Citi's proximity to LaGuardia helps also.
So anyway, if you ever think about trying to pull it off I would recommend as long as you got your shit together and can stay on task.