Hi @Gabe Fernos,
When you say your home won't cash flow well, what do you mean in $$ terms?
Assuming you can cash flow to some degree on the property, I would consider the followin:
1. If you have PMI on the property currently, consider getting that removed via refi.
2. As long as you live in the property, you can take a HELOC on the property up to full value and use that money as a down payment + reno on your new place. Say you pick up a multi for $400k and live in half, you'll likely be able to put 5% down and have plenty cash left over for renovations if needed.
3. If the market is that competitive, surely you should be able to rent it out with little difficulty.
4. I would look at you entire portfolio when it comes to how much you could make. Meaning, if you can keep your current property and get a HELOC, you avoid the selling transaction fees and get access to the most cash. When you combine the fact that you will be renting our the other half of a duplex with owning your current property, you'll probably find that your monthly payments will fall on a net basis while growing your asset base.