The threshold you are talking about should be the least of your worries and is something you can't afford not to have; do you want to gamble $150 vs $2,500 of potential disaster?

I think you may be gambling a bit on what your future buyer may or may not want...For Example if you get a lot zoned for multifamily and develop plans for a 5-plex and your buyer comes in and his plan was to build an 8 unit apartment... 

As an owner, they would be able to cut a deal with a renter if they wanted to take that gamble for some specific reason (i.e. if it was january and the tenant had a big refund coming).

This is because we have agents and sellers who're gambling with the current market and trying to attain REHABBED property sales numbers.

Im not suggesting anything about your intentions but it should be mentioned that lending is no longer comparable to gambling. 

Buying a property that you know would be cash-flow negative from the start is gambling on appreciation.

Off shore drilling?

Yes, I still work full time Offshore and have a full time property manager for when I am gone.

If you go into a deal with speculation of "appreciation" and that's your focus, then you are gambling IMHO.

This gives you a better chance to have enough equity to refi five years out. 25 year amortization would likely leave you "upside down" in five years unless interest rates remain at historic lows (not likely - never gamble!).