The funds in this IRA are currently sitting as cash. I have an IRA that has stocks but I haven't used that money yet. if I take the distribution do i have to do it before 4/15/2019?  How many times can you do this without penalty during a 12 month period?

Clarification- I haven't used the cash yet.

It doesn't matter what form the money is that is in your IRA, stocks, cash, etc. What counts is when you take a distribution. Once you take the money out, start counting the 60 days.You can take a distribution any time during the year.
You have 60 days from the date you receive an IRA or retirement plan distribution to roll it over to another plan or IRA. The IRS may waive the 60-day rollover requirement in certain situations if you missed the deadline because of circumstances beyond your control.

IRA one-rollover-per-year rule
You generally cannot make more than one rollover from the same IRA within a 1-year period. You also cannot make a rollover during this 1-year period from the IRA to which the distribution was rolled over.

Just to confirm, if I am taking the distribution from the same IRA that is sitting as cash, and, stocks, can I repay myself into the same IRA within 60 days to pay myself back?

Yes.

why do you need cash for 60 days and why will you have that cash back 58 days from now.?
Never understood this.

Maybe OP is getting a bonus check?  A tax refund?
IRA loans are not permitted under law.

tax refunds can be delayed or offset, as anybody here can attest