@Evan: OK. I think you should slow down. Below are some of my reasons, and they are direct, so please do not take offense.
First, when I read "I have a financial backer so I can tap $500k.", that tells me that YOU do not have $500K. Your financial backer has $500K. Big difference. Have you asked what the financial backer thinks of your idea? What is his/her expectations (in terms of capital security/preservation as well as yield on capital)? Is this backer going to be a partner and share equity or just a money person? What are the terms for this $500K?
Second, look at your track record from your stated past. You LOST IT ALL. It reads like you went all in and did it too fast. Maybe lost a little focus too. It was one hell of a time. I would slow down, focus and strategically purchase quality deals. You also want to build a team if you are planning on growing.
Third, when you find a bank that will give you a 90% LTV on an investment property, please let me know. You will at best get a 75-80% LTV on your first few, then after that it will get progressively harder. Once you get over 5, some banks will not even look at you. Reach 10 mortgages, most banks will shy away from you unless you have a good relationship with them.
In closing, I would leverage your ability to purchase in cash. I would start by looking for a quality property in your target market that hopefully has a motivated seller. Offer all cash, 5-day DD period and 15 day close. You WILL get a very nice discount. Once you close, make the property "Gucci" and then get a solid renter in there. Start a dialogue with a banker showing him/her what your business plan is. Season the property for 3-4 months, then do a 65-75% Cash-out ReFi. Rinse repeat. This is not theory on my part, it is experience. On June 28th, I just closed on my 3rd property this year using this model. For me it is WAY safer, still have good cash flow, good CoC ROI, albeit slower. If 2008-2010 demonstrated anything, the RE business is not a sprint, it is a marathon.
I hope this helps. I wish you success and please keep all of us posted on what the outcome was.
Joseph M.