I can't offer much in terms of knowledge and experience but can definitely offer some encouragement.

STR's don't care about what they can't see, and meanwhile, I can take my time to do it right.You will be focused on customer service, which is not like a traditional property manager's job, honestly (I've been PM'ing for 20 years so I am aware of what goes on).

The listing agent encourages the seller to accept your lower priced cash offer because the agent gets a double commission of ~5-6% (whatever's negotiated) instead of a higher priced FHA (not sure thing) offer or whatever.

This is very encouraging!

All of my adult working life I've been stuck and complacent in the customer service/retail/sales industry (not the rewarding kind of sales).  

Of course, you will have underwritten the deal at sufficiently conservative financing rate - like the BoC posted 5-yr, fixed-rate reference - that the business easily throws off cash at the actual financing rate.If you are disciplined enough to apply the "cash-back" directly to the mortgage principal as a pre-payment (some lenders will {strongly} encourage this approach) it is a good thing ... if you use the cash-back on a rental property financing to pay-down the principal on your primary residence (where mortgage interest cannot be deducted as a business expense) you may warrant extra kudos.If you are certain you can re-invest the cash-back and earn a higher {net} return than paying down your mortgage financing {particularly that on your personal residence which is paid with after tax income}, the cash-back can be a good thing.  

If anyone has leads on properties that would be good candidates for a rehab, buy and flip project or any advice and words of encouragement we would gladly appreciate it. 

I encourage you to ensure that you know and understand all requirements for renting in the City and that you hire a property management company to represent you. 

If you would like for us to help evaluate a deal, and in your case a property(s) for you, I would encourage to give as much information as possible.

I would strongly encourage those with adjustable rate loans to take a serious look at how their investments might turn out if interest rates rise substantially and rents remain flat.