I too received the August 25, email announcement of faster processing timesI previously predicted  Sept. 9 or 10, due to the Labor Day bank holiday, as to when I would actually receive rent payment, based on previous 2 months experiences and the money was in bank today September 8, which beat my expectation.

Financing your deal is only important to predict Cash flow and overall Rate of return on investment.

The cap rate does not predict cash flow or profitability, only the markets perception that the lower cap rate will be less risky to collect the same NOI.I'm between the Aquarium and the Outrigger Canoe Club now next to Jimmy Buffet's new place.  

I never found a cohesive secret to finding great tenants there, other than "older people" was maybe the closest, BUT it sounds like you have a good or great IT job going, while I applaud your wanting to jump out on your own, be your own boss, etc and say to keep thinking that way, I'd HIGHLY recommend saving up a lot more $$$ reserves first, unless maybe as @William Hochstedler mentioned above, your the 1 in a 1000 superman, but that's hard for anyone to predict for themselves. 

You can never predict when something goes up or down in software/internet.

We think demand and the increase in housing prices is going to slow (perhaps its why we are selling an option), so we figure the house may only be worth $108K in two years ... and we decide to set our option premium to be $2500.00.If our predictions are close, then in January 2018, the house is worth $108K, the option holder exercises his option and purchases the house for $105K ... plus his option premium for a total of $107.5K and everyone is happy.  

I know can't predict the future etc. or bet on depreciation, but it seems like I'd be buying into a high point in the market which of course is never good. 

There are people that think properties will go up forever (It's called "Irrational exuberance")I can't predict the crash (3 years maybe, probably farther away than most people think) but it will come and there will be millions of houses on the market where the owner could not sustain the negative cash flow through the down turn.Pick a market where you get MAXIMUM APPRECIATION AND MAXIMUM CASH FLOW.

What kind if return are you predicting?

I predict  there will be a lot more seller financing opportunities on NYC multi families in 2016.