In other words, my current real estate knowledge is only just scratching the surface.I am exploring real estate because I want the choice and flexibility to spend my time how I choose to. 

For something like that, either the property is close by for weekend getaways, the owner has a lot of time to stay at this second/vacation home, or just has money to spend.

I wouldn't spend a lot of money or time on this unless it becomes an ongoing problem.For me the bigger concern would be the lack of a meter for common area expenses.  

Veronica when figuring out where you want to spend your $100k you'll want to check out The Ultimate Guide to Grading Cleveland Neighborhoods. 

She is willing to get back into (actually spend 750hours/year) it if it will signficantly reduce our tax liability.

Depending on municipality, that addition could cost you thousands in the further when the city finds out. 2) I’d only spend 45k down if I were getting over 8k back in my pocket on year 1. 3) It doesn’t even sounds like you’re getting a “deal” at all with your friend discounting you 5k.

You can't invest if you spend every dollar that you make. 

Even with requesting odds are 1-3 of them will forget each month.  1, no problem.  2 or 3 forget and now you have to spend time figuring out who paid/didn't pay. 

Because spending on in-store groceries surpassed spending on dining-out during the Covid-19 pandemic.

But who is going to spend the time and money to fight that battle?