You should look at doing them simultaneously so that you ensure refinancing the first property won't harm your ability to qualify on the purchase of your new home.Even with a current rate of 3.5%, there's a decent chance that your overall effective rate including the mortgage insurance is in the mid-4's.

As for the Investor/ Realtor question I would like to do both simultaneously.

Karen, If you are in Tampa, there are several title companies here who will do simultaneous closings, where you will not have to bring any cash to the closing table when wholesaling an REO.

I was thinking I could eventually start with small scale projects like flipping houses for a few years to get my feet wet while simultaneously networking with other investors.

What do you mean when you say "3 separate loans under one HELOC simultaneously"?

Simultaneously I try to analyze 1-2 properties per day to get a feel for the type of returns that can be expected from a particular neighborhood. 

However, it also makes sense to do it simultaneously. 

Can anyone recommend a solid tried-and-true strategy that will allow me to do both simultaneously.  

You may be able to get 2 of them simultaneously from different banks for $15-$20K.-0% intro rate balance transfers.

I am simply marketing the deal simultaneously.  3.