I know there are a lot of things that have to happen for this to actually play out on the side of getting rid of STRs, but if it is going to happen anywhere, I believe it will definitely happen on Molokai.

What softwares/tools do you use and what has your past experience taught you that im glossing over?

With decades of experience I can say the vast majority of "cash-cow" properties I, my clients, associates and friends have had started off with minimal to near 0 cash-flow.

Combining my experience as a guest in cabins with some knowledge as a manager of a few houses with them:1 - Patio. 

Just wondering if anyone has experience or feedback about a company called Pillar & Peak Restoration.

I had a horrible experience with Guesty for hosts.

These communities often feature amenities such as fitness centers, swimming pools, and communal spaces, providing residents with a high-quality living experience without the burdens of homeownership maintenance.Moreover, the low housing supply in Sunbelt states has created an opportune environment for BTR developers and investors.

I personally have had great experiences in Cleveland and Columbus. 

Another reason I am looking to DIY this is for the learning experience as well.

I feel like Harrisburg and Allentown preform more like Philly very street to street but Reading is much more consistent in that respect while Lancaster is the appreciation play