Well, I played an OOTP Historical League solitarie through to 1984 with a 1961 starting season and had a blast (you have an option to have the auto-play run for a week, a month, even a whole season), and won 5 World Series and lost 2 of them in that 24 year period.
I have started over making a major change: I felt like the rosters - of good teams at least - had too many very good players on the bench, something that by the way appears to work against a team. The logic is probably similar to that of WIS: value on the bench doesn't help your team, but since there are no salary caps the competition may have higher or lower overall roster value and by big margins (like in RL baseball).
So I went back to 1961 with a new league but added four expansion teams immediately, shutting off the automatic expansion in historical years function. So we started the 1961 season with 20 teams (I added the Memphis Suns - a tribute to Sun Records, and the Seattle Mariners to the AL and divided the league into East and West Division with a best of 7 championship series, and then added the New York Mets and the Denver Rockies to the NL doing the same divisional divide and playoff set up.
So although when you turn off the minor leagues you automatically have a reserve roster that goes up to 15 players, most teams had a total roster of around 28 or so, maybe an extra pitcher or two, a utility IF or OF or a third C on the bench, nothing more, since we were stretching the available players over 20 teams.
When the number of players grew by 1962 we had better overall rosters, but it was still more difficult to accumulate a whole bench of stars as had been possible in my previous league.
But I am thinking of expaning again in 1964 , and running an expansion draft,, and maybe even of limiting the number of safe players to smaller than the usual 15 that is the default setting, because, although I was overjoyed to win the World Series in 1963 with my team, I still see weakness in the solitaire game:
When you hold an inaugural draft for a new historical league, you have to either pick individual players for each team, which I confess I am too lazy to do, or you pick only for your own team, and you let the auto-draft draft for all the others by clicking "auto-draft until the next pick by (name of your team)".
When you do that, the auto-draft picks the best players to be sure, but I think the criteria it uses it a certain balance between players that are immediately good and long-term ones and it also goes straight for position players, mainly hard-hitting OFs.
So I, in the 1961 inaugural draft went looking for long-term value, figuring the 1961 season would be a wash (we did pretty well actually, ending with a .500 record that year, then losing out in the division race in 1962 on the last few days of the season before winning the WS and going 100-62 in 1963. We are about to start the 1964 preseason now).
So I ended up with Bob Gibson, Dean Chance, Gaylord Perry and Sam McDowell. In the 1964 draft I got Clay Carrol and Jack Aker, so my team, with Boog Powell at first (again, going for longer-term value in 1961), Frank Howard, Brooks Robinson, Lou Brock and Tim McCarver will be very hard to beat for a long time.
A dynasty will be enjoyable, but I also want a challenge, so I am leaning toward adding two more teams, running an expansion draft, having to lose a few of these stars and in general reducing overall league roster quality again, to keep it interesting. So trade will not be good player for future great player, but will mean giving up value for value (I always set trading on "hard" anyway, but still do get steals for some reason occasionally, though other times you can't give away a good pitcher for a third backup catcher or fifth OF, who knows?).
More soon. Oh, and the Twins' Willie McCovey broke Babe Ruth's single season record by hitting 61 home runs in 1961.