Did you just save up from a 9-5 job or pull money out from number 1?

If you bought them cash, I would seriously consider pulling the cash from at least one (assuming it still has healthy cash flow after you do) and look for the next deal, given that you want to live off this income eventually.

You may argue the prices are going up fast in your market, but the market has been hot and is due for a pull back at any time.

I was able to get myself in by finding a specific goal for my first property and pulled the trigger when it came along.

But my question/problem is....When will I know to pull the trigger and purchase that first flip?

I finally pulled the trigger and put in my first few offers but haven't had any luck yet.

I have been going through it pulling the addresses that meet my criteria and generating a new list to be skip traced. 

Your other option is to pay a little more and pull a list of 1000 homes that actually meet your criteria, and mail to them. 

It now sounds very difficult to pull that off.

@Nick Stangowhile it can be possible to pull your personal funds with the funds of an IRA in a joint investments under certain circumstances it is very easy to commit a prohibited transaction with this arrangement.