You can do multiple Trustee to Trustee transfers in the same year. There is no penalty for doing this. Just ensure that it is a direct transfer. There is a limit of 1 rollover from a Traditional IRA to another IRA in a calendar year.
The one year limit does not apply if:
1) rollover is from plan-to-IRA rollovers
2) IRA-to-plan rollovers
3) trustee-to-trustee transfers to another IRA
4) plan-to-plan rollovers
Here is the IRS link with more information on this:
https://www.irs.gov/retirement-plans/plan-participant-employee/rollovers-of-retirement-plan-and-ira-...
