Just a boy and his digimon
Getting to 1 year of in-game time is a medal that is a pure waste of time. The only thing you can do is rest or train for no reason until you hit one year. That would probably be at least an hour of just resting. Also, the medal for catching 100 fish certainly wouldn't be very interesting to watch. An hour of fishing would be almost as bad as resting. It seems pointless to only collect some of the medals, though. It would feel incomplete to call it a 100% game and say "look, I collected all of the medals (that I thought were worth it)" and then show off your half-full medal collection.
So, personally, I also lean towards just prosperity points, but I didn't want to say what my opinion was on the matter before getting some other perspectives, as I didn't want to bias them with what I would like it to be.
Monzaemon can take on pretty much anyone when he is freshly digivolved if you have the right number of small recoveries . And as for the sanctuary, I can safely say that he can. I originally put ice sanctuary in my test run, but I realized that it requires multiple battles and is out of the way from everything else, so I scrapped that idea. But, I did successfully do it with Monzaemon, so he is definitely allowed in. Digivolving to Monzy is very difficult to do without the Monzaemon suit, though. So, in order to do it inside of the mansion, you would need to train up numemon. He actually receives fewer points from each training session and would take longer to turn into an ultimate than just about any other digimon. Worse than that: there's no guarantee he would survive long enough to become an ultimate. Theoretically, you could throw all of your chips at numemon, but that means you would have to win battles as numemon to get those chips, which is near impossible, because numemon is useless. And throwing chips at numemon would hurt my soul a little.
On the other hand, raising Greymon is an interesting idea, but still leaves the problem of needing numemon in order to get to Warumonzaemon. They only open the doors for Monzy.
As for HalfMillennium, that plan also seems very solid. The only problem is that your plan requires both getting Monzaemon and then training to get a full-fledged Giromon. It seems like, if you couldn't get it done with one digimon, then the Mysty Egg would make for a sufficient virus ultimate without needing to train at all. Using the item could cut off 15-20 minutes of training. Also, using Hairgrower could help cut additional time off getting Bakemon.
Furthermore, your plan gets two vaccine ultimates, rather than one vaccine and one virus. Beating Skullgreymon with Bakemon could be even more difficult than beating it with Digitamamon, in addition to taking longer. I'm really sorry that I keep disagreeing with you. Personally, having played this game as much as I have, it always feels wrong not training my digimon so I understand why you feel like training is the best option, but I do believe that it is faster not to, so I am trying to go against my instincts.
And, I think that your definition of 100% seems reasonable. If I was the one doing it, I think I'd be up for the challenge of beating both Machinedramon battles. The only problem is that, I think that he has max stats and is supposed to only take 1 damage from your hits if you don't have 999 strength. So, it might not be feasible without a crapload of extra training. But, if it can be done, then I'd be game.
So, personally, I also lean towards just prosperity points, but I didn't want to say what my opinion was on the matter before getting some other perspectives, as I didn't want to bias them with what I would like it to be.
Monzaemon can take on pretty much anyone when he is freshly digivolved if you have the right number of small recoveries . And as for the sanctuary, I can safely say that he can. I originally put ice sanctuary in my test run, but I realized that it requires multiple battles and is out of the way from everything else, so I scrapped that idea. But, I did successfully do it with Monzaemon, so he is definitely allowed in. Digivolving to Monzy is very difficult to do without the Monzaemon suit, though. So, in order to do it inside of the mansion, you would need to train up numemon. He actually receives fewer points from each training session and would take longer to turn into an ultimate than just about any other digimon. Worse than that: there's no guarantee he would survive long enough to become an ultimate. Theoretically, you could throw all of your chips at numemon, but that means you would have to win battles as numemon to get those chips, which is near impossible, because numemon is useless. And throwing chips at numemon would hurt my soul a little.
On the other hand, raising Greymon is an interesting idea, but still leaves the problem of needing numemon in order to get to Warumonzaemon. They only open the doors for Monzy.
As for HalfMillennium, that plan also seems very solid. The only problem is that your plan requires both getting Monzaemon and then training to get a full-fledged Giromon. It seems like, if you couldn't get it done with one digimon, then the Mysty Egg would make for a sufficient virus ultimate without needing to train at all. Using the item could cut off 15-20 minutes of training. Also, using Hairgrower could help cut additional time off getting Bakemon.
Furthermore, your plan gets two vaccine ultimates, rather than one vaccine and one virus. Beating Skullgreymon with Bakemon could be even more difficult than beating it with Digitamamon, in addition to taking longer. I'm really sorry that I keep disagreeing with you. Personally, having played this game as much as I have, it always feels wrong not training my digimon so I understand why you feel like training is the best option, but I do believe that it is faster not to, so I am trying to go against my instincts.
And, I think that your definition of 100% seems reasonable. If I was the one doing it, I think I'd be up for the challenge of beating both Machinedramon battles. The only problem is that, I think that he has max stats and is supposed to only take 1 damage from your hits if you don't have 999 strength. So, it might not be feasible without a crapload of extra training. But, if it can be done, then I'd be game.