Trade Logic means Everything

The IWM is a terrific underlying for intraday trades. Before I started trading it I had no idea it moved "so much", "so much" being "enough for a trade". I trade it almost daily.

I have March puts on IWM that because of how wild the IWM has been in the EOY party, are pretty far OTM, 128 strike. Nevertheless, I've been able to sell against them well over a dozen times and buy back sold puts. Yes, they have been higher strike puts, necessary of course because there is almost no premium left in 128 puts. If I left the position on, it would be legging into a guaranteed-loser credit spread but I sell the upper puts with the direct intention of buying them back. I won't take over a dime loss on them. This is a bit like you have described financing your short positions which today might be underwater.

It's also not especially risky IMHO to sell naked IWM puts 2 points OTM. No, you can't sell them and walk away.

I have had a couple of days where I have been able to sell puts against my longs three times and buy them back three times, for 20 or 30 cents a whack. Not dramatic, but chip, chip, chip away. VERY often I can sell them and buy them back twice in one day.