It is a gamble for both parties, but a good solution if the seller has no equity.Florida homes may depreciate as some of the other sand states, like CA, NV and AZ.Offer to pay minor maintenance to entice the seller, but only 1st 100 dollars or so.

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.

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. 

Investing was not at the forefront and when I returned it took some time to settle back into normal life.Fast forward to 10-2013The day job was really taking it's toll on me stress wise and re ignited my passion for REI again.

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

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