I have to look off-market because inventory is extremely low here.

The home office deduction is a popular deduction that people try and be aggressive with but in my experience it is extremely difficult for people to qualify for when everything is done by the book.

There's that pickle.You can raise up the whole house on piers, but expect it to crack and settle.You can build sump pumps and automatic Moen water sensors to trigger the pumps but if the water rises fast it won't save the ship, and power will probably be out so you need a generator.Do not expect or plan that anyone will fix the seawall, it's on you and the problem is will your neighbors all have millions of dollars to fix at the same time that you need to?

The way people quit their jobs is by hustling extremely hard, building a few million in sweat equity through flips/BRRRR/value add, and then dumping it in cash flowing assets that are lower maintenance. 

she has enough equity to sell the home and profit, so advising her to file for BK is kind of extreme, am I on the wrong?

If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Frankly it doesn’t seem like you’re ready to pull the trigger on this deal. 99 out of 100 “deals” from wholesalers are bad IME.

This was my first deal and I suffered from analysis paralysis for two years before pulling the trigger on my first real estate investment.

As was mentioned earlier, it is extremely difficult to find cash flow, especially in our market (charlotte metro). 

@Ellie Narie we don't manage Class D rentals because they are extremely difficult to manage.Yet, owners are unrealistic and expect Class A or B results from them!