With the cosmetic stuff I would be gambling that higher rent to help cover the eventual HVAC and windows, or a BRRR to take cash out.I don't expect the seller to take the offer.

You should be shooting for at least $100 per month per door in real cash flow.Of course none of this takes into consideration the appreciation game/gamble or amortization, however, if your goal is income, you need to be fully educated on operating expenses and all other costs associated with owning rental units.

How about the old and occasional appreciation misspelled as "gambling".

Depending on the rental market there raising the rents could be a gamble.

Off shore drilling?

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

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

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!).

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

In addition I have 3 of the best off shore providers in my camp as well.