When did Paul first preach a gospel of Gentile liberty?

According to Paul (and others), Gentile men who accepted Christ were part of the people of Israel without having to be circumcised. Now, I used to assume, with the majority, that Paul preached this message from the start of his ministry, soon after his conversion. However, a recent lecture by Gerry Schoberg has caused me to dismiss this assumption. His conclusions are a little different from mine but can be found in his new book, Perspectives of Jesus in the Writings of Paul PTMS190.

Thesis
The first preaching by Paul to Gentiles that we know about is during the "first missionary journey" in about 46AD, yet Paul's conversion was in 35AD. Here I argue that Paul did not preach a circumcision-free gospel during the intervening 11 years.

Evidence
1. If Paul had established Gentile churches in this time period Acts would have said so, since Luke is very interested in the spread of the gospel to Gentiles (see Schoberg p119).

2. We have no surviving letters of Paul to any churches that he established in this time period (see Schoberg p119).

3. The church of Jerusalem sent Barnabas to Antioch after hearing the news of the conversion of many Gentiles there (Acts 20-22). If Paul had already established Gentile churches, why did Barnabas not visit them instead?

4. Barnabas found Paul in his home town of Tarsus (Acts 11:25), which is where Paul had gone years earlier (Acts 9:30). This gives the impression that Paul had remained there, perhaps because he had family and friends there.

5. The controversy in the church about circumcision arose only in ~48AD when men came to Antioch from Judea. If Paul had been establishing churches of uncircumcised Gentiles  ever since his conversion in 35AD, why did the controversy not arise earlier?

6. Paul went up to Jerusalem (in ~48AD) 14 years after his conversion and presented his gospel of Gentile liberty to the church leaders there (Gal 2:1-3). He did so privately because he was worried that he had been running in vain. Why did he take 14 years to check that he had not been "running in vain"? Why did he not make an earlier visit to Jerusalem to discuss the issue? Why did he not present his gospel to them during the famine visit (Acts 11:29-30; 12:25)? John Chrysostom notes, but does not solve, this puzzle:

What is this, Paul? You would not consult the apostles at the beginning or after three years, but you now consult them after fourteen years are past, to make sure you are not running in vain? Would it not have been better to have done so at first, rather than after so many years? And why did you run at all, if you thought you might be running in vain?

 It makes little sense if he had been preaching that same gospel for all those years, but it is perfectly consistent with the account of Acts. According to Acts Paul had been on only one missionary tour before he laid his gospel before the Jerusalem church leaders. The Holy Spirit had commissioned Paul and Barnabas for that tour, so he had no opportunity to check that Jerusalem endorsed his message. His uncertainty about what Jerusalem believed would have been heightened when the men who came from Judea claimed that Jerusalem supported their view that Law-observance was necessary (Acts 15:1,24).

7. Gal 1:23 reads 'they only heard it said, "The one who formerly was persecuting us is now proclaiming the faith he once tried to destroy."' Now, the faith that Paul had tried to destroy did not include a circumcision-free message (Peter's Cornelius episode came later). Paul makes no distinction here between the faith that he proclaimed early in his ministry and the pro-circumcision faith of the church of the time.

8. Gal 5:11 reads "why am I still being persecuted if I am still preaching circumcision". This may refer back to a time earlier in Paul's ministry when he had preached circumcision to Gentiles.

9. Paul wrote Galatians to counter the view that he believed in circumcision (for Gentiles). The Galatians were thinking that Paul preached Gentile liberty only to please the Jerusalem church leaders. See here. We can imagine how this misunderstanding could have arisen if Paul had not started preaching Gentile liberty until after the Jerusalem church leaders had come to support it. If, on the other hand, Paul had preached a circumcision-free gospel before anyone else did, then it would be surprising that he does not say so explicitly in his letter.

Conclusion
For the reasons given above, we can be confident that Paul did not preach a Law-free gospel until several years after this conversion. His missionary tour of Cyprus and south Galatia with Barnabas was probably the first time that he did so. It is likely that Paul did evangelize Gentiles in the early years, but he did not preach against circumcision at that time.

When did Paul first receive his circumcision-free gospel?
What, then, are we to make of Gal 1:10-12?

Or am I trying to please men? If I were still pleasing men, I would not be a servant of Christ. For I want you to know, brothers and sisters, that the gospel that was proclaimed by me is not according to man; for I did not receive it from man, nor was I taught it, but I received it through a revelation of Jesus Christ.

Paul is challenging the rumour that he opposed circumcision in Galatia only to please men (i.e. the Jerusalem apostles). Paul therefore points out that he had received his gospel of Gentile liberty by revelation at his conversion. At least, that is how he interpreted the revelation in retrospect, it seems. Why, then, did he not preach that gospel from the start? Well, we know from Gal 2:2 that it would have been futile for Paul to preach Gentile liberty when the rest of the church did not yet support such a view. Paul could preach against circumcision only after the Jerusalem church became supportive of that view, following Peter's vision. The church of Antioch was the first to include Gentiles in large numbers (Acts 11:19-22), and it is interesting that at that time Barnabas recruited Paul to come to Antioch to teach (Acts 11:25-26). Presumably Barnabas knew that Paul would support the steps that Antioch had taken to include Gentiles.

I propose, therefore, that Paul received his gospel of non-circumcision (at least in some respects) at his conversion, but did not preach it until much later. Many will object to this. They will use passages such as Gal 2:11-14, 5:2-12 to argue that Paul was uncompromising in his opposition to circumcision and would have preached against circumcision from the start. However, they fail to understand that Paul wrote Galatians to correct the view that Paul actually believed in the need for circumcision. Paul takes an extreme position in these passages only to correct the Galatians' view that a) he believes in circumcision and b) he is writing only to please Jerusalem. Interpreters have become victims of Paul's rhetoric and have cast him as a heroic, principled, individual, rather than as a first century team player who belonged to a collectivist culture.

Imagine a parallel universe in which the rumour in Galatia had been different. Imagine that the Galatians had accused Paul of being a maverick who was stubbornly uncompromising and unwilling to collaborate with other church leaders. Paul would then have written to the Galatians to counter that misinformation. He would have given evidence of his close co-operation with the Jerusalem church, and subsequent generations of commentators would have come away with the view that Paul was a sycophant of Jerusalem. We cannot understand Galatians without first discerning the misinformation that Paul writes to correct.