I think all the other seasoned investors would agree the best timing to make your first step into REI is yesterday.  

Please, please, PLEASE learn how to underwrite an apartment before taking the next step.

We have done tons of non-occupied flips too (fast method).

It’s awesome that you’re taking steps toward buying in an area you love and planning for the future—whether it’s as a second home or a long-term investment for your kids, this is a meaningful goal.

I love how you reframed failure as a stepping stone to success.

Giving them a laundry list of items will typically just overwhelm them and create more confusion instead of giving them a smaller step process to get more confidence to get the ball rolling and then they can get into the weeds on their state when they get the contractors out there, have local bids come in, and dial in their plan. 

I feel like it would be great to trust a property management company on all of this, but it would be hard not to step in if you could do a better job at screening bad tenants (eg screening HUGE future problems).I initially managed properties myself, but now I delegate that responsibility to my business partner, personal assistant, or a property manager at my brokerage.Most PMs I know will send you an applicant for final approval and you can get on the phone with them and ask them questions

Your problem is probably your method of wholesaling. 

WE also make sure our driveways are 4 feet wider than Lennar this way when they step out of the car they land on concrete NOT dirt . 

Perhaps they invited Jerryll based on his extensive SEO knowledge and did not look into his questionable marketing methods and extremely high course pricing at $5800 and $19,800.