2- Let's say, I buy a second mortgage and lis pendens has already been issued for the first mortgage and an auction date has already been set for it.

In addition, there is a separate issue if you lost your principal investment.

You can guess based on last year and add or subtract any changes, but that too comes with issues.

@Benjamin WeinhartMy experience on this tax forum tells me that highly technical discussions of the Code/Regs nuances are not well suited for this platform.That said, my 2 cents is that this issue is a matter of interpretation.

I would also join local FB groups and meetups to learn specific issues that folks in Philly deal with.

There is no issue that I can think of regarding taxes.

Seems like it’s one of those item where if you don’t spend real money (well over $1K) then there are issues with warping.

I am writing to seek clarification regarding the insurance claim check that was recently issued to me as the payee, with both my personal name and the mortgage company's name listed.

I have not had any issue so far. 

We’re three weeks in and 6/10 houses are ready to go and the others have issues that would have delayed the package.