Hi. Apologies if this gets complicated, I will do my best for it not to. The high-level idea is for me to spend the holiday season in St. Petersburg, Russia, but I'd like to make a stopover in the U.K. on the way. The important dates are as follows:

12/18 - earliest I can leave
12/21 - have to be in Manchester for my two favorite teams' match (MU-WHU)
12/22 or 12/23 - get to St. Petersburg
1/5 - latest I can fly back

Points to spend:
Marriott: roughly 50K
American Airlines: 47,xxx
United: 62,xxx
SPG: 11,xxx
Delta: 21,xxx
Avios: 4K
Flying Blue: 5,500-ish

The flight back is the least of my worries. I can grab a business-class one-stopper from Helsinki for 50K United miles plus $70 or so. Where it gets complicated is in the first leg of the trip. So far I have two clearly identified options:

1. 20K Economy MilesAAver (the transatlantic bit)

Leave Dec. 18 or 19

AA 2810 (9:05-10:55 DTW-LGA)
AB 7451 (17:40-6:55 next morning JFK-DUS)
AB 8746 (15:20-15:40 DUS-STN)
Train to Manchester
Watch the match
Either go back to London and take a direct BA LHR-LED flight for about $350 or one-stop from MAN (via most likely Helsinki) for around the same $ or another 20K points (business class)

2. Around $600

Leave on same dates, 18th or 19th.
Somehow get to Chicago
Fly Aer Lingus 1-way to Dublin
Spend a day in Dublin
Somehow get from Dublin to Manchester (probably also on Aer Lingus)
After that - same as option 1, but most likely back to London for a day.

Option 2 is a bit more fun as I've never been to Dublin before and helps me avoid flying in a CRJ700 and a DH4 (there's just something about small planes I can't stand), but it costs more actual cash. Obviously, neither is a particularly graceful solution, but that's why I am asking the collective wisdom of FT in hopes you guys might find a more creative way. Getting to 50K miles on AA would get me a few more options in business class (and potentially one fewer connection), but I'm not sure I want to gut my entire account.

Advice on budget places to stay in England/Ireland is also much appreciated.

I am also not entirely sure I understand how the Saver award works with AA and if it's possible that flights that aren't available on it right now might open up later (in particular on BA as those options seem to be few and far between) and whether or not it's worth waiting a month or so to book.

So, all told, many more questions than answers, but the community has been amazing in the past, so here's hoping for a few better solutions. Thanks!