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.

The lady on the phone sounded confused and said" investing?

I don't know much about the lady or her program but the key concept in wholesaling is finding a deal where you can enter for less than you can exit, thus creating an arbitrage between your purchase price and your sale price.

"She is a very pretty young lady.."

It's great to list some points as to why selling direct may be beneficial, but CRE owners will be a lot more numbers-savvy than wholesale a SFH from a little old lady. 

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.

So ladies and gentleman this is what I have so far.

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... 

I had a cleaning lady I would pay $100 - $120 per day 3x a week but she would take care of laundry and averaged 2-3 listings per day.