In other words, I already have tenants for the 2023-2024 school year and I'm now getting ready to market my place for 2024-2025 and expect things to get busy in the next month once classes start.

They will generally meet you at the property and walk you they what they expect. 

*My future wife is supportive and would be including her income to DTI calculations as well as potential savings.

In general I would expect to pay more for an insurance on a business policy rather than a personal policy and am not surprised by the increase. 

It's normal to feel a mix of excitement and nerves – it's all part of the journey.With your short-term rental in NY no longer an option, flipping could be a solid entry point to build up some capital for future ventures like buy-and-hold properties.Choosing the right market to start is key.

I have started screening after the realtor screens them and tell the rules, setting expectations upfront.

If you are not quite ready then you can do a lease option where the majority of the lease payments will go towards your downpayment that will be applied towards the "future purchase" two or three years down the road.

Before we get started I am upfront with them on expectations.

Establish an emergency fund, manage your debt, and save for a down payment to lay the groundwork for your financial future.

If you sell "as is," maybe you lose less money now, but if the place could grow in value or you think the property has good future, keep it because this might give more profit later, even when there are problems now.