I have begun writing down my next 3 tasks to do to turn the whole process into a series of bite-sized steps.

Pull the existing comps based on similar size and age.

It's good at a minimum to have a very short list.  3 out of those 4 you can probably select prior to purchasing something, the contractor piece is a bit more complicated depending type of project & size, you may be dealing with different contractors. 

I have great relationships with him, referring other clients, and he always shows me how to do it right way, and I already did multiple things by myself - making window screens, painting of 8 interior doors in 2 days, hardware for kitchen cabinets, replacing bathroom faucets etc.

If they refuse, evict them and get them out.You may also considering screening all your current occupants to clean out any drug dealers, sex offenders, etc.

Some will if the owner of the property is the LLC and you rent from the LLC.With the size of your portfolio, you will find some of your best options with combining your Homeowners with the rentals, auto and Umbrella.  

Does the realtor also carry out credit checks and screenings?

Tub/shower caulk & window screens!

Now you need to start preparing for marketing, showing, screening software and processes, selecting a tenant, Fair Housing, emotional support animals, collecting a deposit, disparate impact, local and state housing laws, Section 8, your lease agreement, late rent, unpaid rent, partial rent, bounced checks, etc.No worries!

Insurance will be paying rent and they say I can screen the tenants myself still.