I'm at a point where I could sell every property and, in a way, start fresh with the knowledge I have now.Here's my thoughts:I sell every property and come out with 1.4m - and that's after paying off my debt.I then take the 1.4m and invest in multiple (larger) properties with multiple doors.

A freshly renovated property is likely to get more money than one with a tenant living in it. 

Maybe fence it off and make a garden.Feed you family free fresh fruit and vegetables (organic), sell the remainder on the roadside (pumpkins in October, melons and corn in the summer, peas, green beans, radishes, green onions, carrots, etc...).Sell from a trailer.Use the money for a family vacation.Teach the kids about business, pre-planing (planting hoe-ing gathering), and profits.Just my 2 cents.

I am also open to video calls as well, I just don't have very many people around me in the industry and want to keep my mind fresh with what's current in the market.

And most decisions are written by law clerks fresh out of law school.In PA Tax Upset Sales, the mortgages and all liens judgments, etc are NOT  wiped out, you are buying the property and ALL of the encumbrances.Here's how the court works in the real world, been there many times. 

My name is Prit, and I'm excited to introduce myself as a fresh face in the Columbus Ohio real estate scene.

I’m trying to post something.... but I’m fresh out of virtue signals.

You still need to make it fresh and clean. 

Can a landlord buy the insurance on their behalf and bake it into the cost of the monthly rent to ensure it's purchased?

Yes, FHA has an UPfront insurance premium factored into loan at start with a monthly insurance premium baked into your monthly payments every month.