This health issue ultimately led to a close family member passing and now I don't believe they have any family living in our area anymore.2.

I've had some not happy when I have asked them to split it out.I've tried asking questions to the IRS customer service reps, and didn't have the best luck.While I cannot cite a specific official guidance on this issue, I consider debit cards exempt.

Since the properties are in New York you have a few extra steps you need to do to keep all of your funds out of NYs hands at closing.Here's an interesting BP thread on the South Carolina property tax issue you mentioned. https://www.biggerpockets.com/forums/725/topics/604427-south.... 

This issue, while easy to solve, only came up at the end of the process.

Are you aware of some actual legal authority that validates the IRS opinion on this issue?

Is it a common issue for beginners to get a PM on board with only 1 property to manage to start?

The biggest issue was getting it out of there. $250.

Most take near a year in southern Ca, but you hear of exceptions in both directions on that timeline.What some developers are doing here is leveraging the affordability issue and getting permission to build additional ADUs by designating some as affordable or semi affordable units.  

One of the biggest issues is probably borrower default—whether due to mismanagement, market downturns, or unforeseen circumstances, lenders can end up in long, costly recovery processes.

But if you are saying that is always breaking or giving you issues, I know that can be a make or break.