-BenHey Ben,Usually I am a hard "No" on selling properties you already acquired just because its usually pretty difficult to figure out the financing, but that $140k you would get does sound appealing.

Painted front porch for curb appeal.

This is another way to visualize a similar idea of the waterfall, but will include mortgages or other loans on the property in it.There is no single structure for either the capital stack or waterfall. 

This past tuesday, I've managed to close on the property (Yes, we were on escrow for 2 months due to some problems rising because of Covid-19).As I'm typing this, I still can't believe that I've managed to achieve the goals I have visualized in my head.

Painting and adding window shutters (my idea) will definitely add curb appeal and possibly increase the appraisal.

Out of the three the Virginia highlands property sounds most appealing to me.

If it is even partly true that more people will be working from home, my sense is that providing a nice renovation in a decent area with a yard could be the way to go because you could appeal to a broader spectrum of buyers. 

You can create a checklist of likely locations of bed bug nest for your cleaning person to visually inspect before cleaning the house (they'll probably appreciate not working in a bedbug-infested house).

Do you have any constructive feedback on how to make our appeal stronger and/or our next steps?

He’s probably in his 60s give or take so I’m thinking something like flips or brrrr would appeal more to him since I can pull/make the money back in about 6 months vs a long term play.