But that's fine, RE investor routinely have to try for a great many deals before the right one goes all the way through."

In the multifamily sector I routinely see loan terms of 7-10 years with amortization based on a 30 year schedule. 

Do the potential list of issues make you uncomfortable or unsure of the numbers?

However, the first lender may feel uncomfortable with you not having any personal money in the deal or "skin in the game".Another option that may be even more plausible is to partner with a private lender.

My next line of thinking is owner-financing but I'm unsure as to where to even start.My question: In a hot market like Denver, how does one buy investment property, strictly based on numbers (i.e- property paying for itself), when sellers are routinely getting 40-50k over asking?

If that is someone's intention, to buy cheap, fix cheap and upkeep cheap, yet collect that rent and do their best to not stick anything back into the property, word gets around and the inspector's office can easily make life very uncomfortable.

I routinely sell and buy properties for clients of all kinds.

I agree with you that to be successful you have to sacrifice and be uncomfortable at times.

But for some reason I feel really uncomfortable getting out of my comfort zone going to a very sophisticated market such as Tampa Bay.  

This takes away the uncomfortable feeling if fibbing and also makes it so you dont have to have back out clauses in the event you cant sell it.