Even though, Actual Cash value will result in insuring a lower amount of coverage, partial losses are subject to the depreciation. 

Is it even making sense ?

This is because you can theoretically knock that one out sooner, and then put even greater force against the next highest balance until you've eventually got them all paid off - which is a great goal.

Even with repairs and vacancies, my portfolio has been cash flowing extremely well.

It just so happens that none of the individual expenses exceeded the $2,500 rule even though the aggregate cost to construct a set of cabinets (example) may exceed this threshold.Since 1.263(a)-(f)(6) specifies intent rather than the end result (Unless you think (6)(i) would apply), since the intent of the taxpayer was not to manipulate this election for a tax benefit, my assumption is that they would be able to expense all of the items normally.Just looking for confirmation as I'm pretty confident my understanding of the regulation is correct.

We've considered home equity loans, HELOC, even credit card with high limit and 0% interest for many months.  

This meeting made me realize that it would not be as much as I had originally thought.Despite being willing to work, I was taken aback by this number, because it was not even guranteed. 

Couple with it the dramatic increase in currency in circulation caused by runaway spending by politicians of both parties and you get even higher inflation.

(I do not want to do AirBnb) So I'm okay with even paying a few hundred a month if its acting as a second home, something like house hacking light.

We absolutely plan on meeting with a tax professional to plan this out, but I’m curious if this is even possible before we push to that next step.