Seek a tax professional for more detailed information.  

After thinking on it a bit more, I am going to look into the feasibility of a rent by room strategy to increase the cash flow and speak with some lenders to learn more details about what I'd need to provide to be able to consider these rents in my DTI calculation when I am qualifying for the next mortgage.

A lot of houses have no windows on the South side and that is for a reason.You didn't say where you live but unless it's the far north, I would pick house #1. 200 extra SF is nice too.....If there is not enough sunlight down the road and it bothers you, you can always add a window on the front, or even easier, put in a Solatube in a central location.

Knowing the lease details and tenant situation is crucial for planning your move and managing the property effectively.Overall, your plan seems like a solid approach to kickstart your real estate investment journey.

As an agent, I never charge any extra admin fee, only homes I’ve sent or showed them, and have an easy termination clause if it’s not working out, on either side.

Here's a simplified and effective approach: Gather Information: Obtain details about the property, including its purchase price, estimated rental income, expenses (such as property taxes, insurance, maintenance costs, and property management fees), vacancy rate, and any financing terms (e.g., interest rate, down payment, loan term).Calculate Gross Rental Income: Determine the total potential rental income the property could generate annually.

Be as detailed and specific as possible when mentioning your future plans, current operation/experience level, ongoing projects, etc.

I would add an extra layer of tenant screening by calling previous landlords and their personal references.

Maybe, with different terms and that's up to you if you want to make that extra risk associated with it and how much you feel the other side needs to, too.

Any extra you can use yourself in any way you want.