I look for whole kitchen packages where people are replacing with stainless or newer. 

I would suggest selling all as a package, many investors and people look to house hack are looking for Multi-Unit properties. 

What’s the best way to secure a deal, and not encounter with another wholesaler going after the same property.

Embedded in that software are accounting packages to manage the property. 

When it comes to tax time, Baselane has a feature to download the tax package needed to easily send it over to your CPA. 

As mentioned your biggest challenge is going to be selling the package at/close to same time. 

First I scour past posts to see if my problem has already been encountered (usually, yes) or my question has been answered (again, usually yes).

Because let's be honest, they are always looking for a reason to do so.I'm especially interested to hear from anyone who actually encountered this issue and how it was handled or who works in the homeowners/landlord insurance industry.Thanks!

"December 22 (RECAP) - Received final closing package with all signed documents.

I keep a spreadsheet of every lender/lending company I encounter so I always have someone else I can try if my lender gives me a no: https://www.biggerpockets.com/real-estate-companies/hard-mon...