Everyone here is an adult and can make their own choices.

If you ran your numbers for your property and you still cash flow(after mortgage,loan payment and reserves) would it be a wise choice to do so?

I think a lot of people living in expensive markets on the west coast invest in OOS not by choice, but by necessity and that could be dangerous. the biggest problem I see with out of state is lack of control of the situation if the issues ever come up.

Would it still be beneficial for us to do a cost segregation?

It is their choice to keep the existing leases, written or verbal, and the only thing you can change is the rent.

And also you pick the right choice to start in wholesaling as new in real state business.Here in biggerpockets community you can get more knowledge and strategies to be successful in real estate business.Best Luck for you.

what do you need to make the choice, the current choice as well as the long-term/next or future choice?

If you do things wrong you can lose a lot of money.Your choice is a personal choice which will depend upon your attitude towards risk and your financial ability to handle any surprises.

If quality management software would be beneficial, we would try using it.

So in your case I think what you were saying is that 85sfr at $200/door is your ultimate goal, but is not the amount that you "need" to be FI.Lastly I would never say someone has to live on 60K per year, that is their choice but if they have a desire to achieve FI sooner the lower they can get that "need" number the sooner they can be FI.