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.

This just seems a ridiculous amount of money & a crazy complex amount of paperwork that I have regrettably signed up for ....Any advice or experience in this area would be extremely helpful !

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.What else can we assist you with?

A local RE professional should be able to provide this information to you as well.In New York, we deal with this scenario frequently and oftentimes it does not make sense to legalize ADUs because the permit process is extremely lengthy, the cost is high (sometimes $150-300K for 1 ADU unit), and the potential increase in property valuable is not worth the risk.If you already have an approved permit/plan and can get your renovation down to $80K, you may want to consider this project if the ARV is say north of $800K.** You should also look into any potential property tax increases associated with this change.

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.

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

Land flips for us are extremely passive and we have almost no competition in this niche either..

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.