And many times, buyers end up paying more if they have contingencies, to win against other cash or non-contingent offers, so I often wonder whether I am actually helping my clients by adding contingencies in this market...I try to disclose as much as possible and explain why we need competent lenders and no contingencies, but I can see that many buyers esp first time buyer are skeptical until they lose a couple of properties they loved over non-contingent offers...And there's no monetary compensation received from my lender whatsoever.

But by doing that, I'd be losing about 43sqft of area.

Any suggestions on what to expect or what action I can take if I lose the bid? 

I have lost friends that i consider family and have also seen what happens to the families when they lose the heads of the households when they did not have anything left for them.

Option 1: pay off 20k remod and wait to build up more cash to buy additional SFR but could lose out.

But I also cant afford to lose money.

I guess me and my partner was frustrated that every year we would be losing money on the 2 properties , so we just sold it fast and at a lost.  

Regardless of which State you are closing in, some title companies will and some will not.You lose nothing by asking, but if you don't even ask - - you're guaranteed nothing will happen.

There are people, this very moment, that are losing money from real estate month after month. 

I was working with a couple investors, who bought cheap properties that wouldn't pay my ledger balance, let alone my bills, and struggling to list homes after losing the builder I worked with at the beginning of the bubble burst.