It’s okay to have opinions and personal values, but I think it’s stupid to let that limit your own ability to make money.

We have been renting this out as a short term rental on Air BNB which has covered costs, but we have a somewhat unfavorable debt structure on it that limits our ability to cash flow and/or extract equity from the asset.  

My worry is the ability to cashflow with prices being what they are at this moment.

The thing with retail, to me, is it is much more about the tenant and their ability to run a business than it is the real estate.  

Afterwards, you want to then inquire about the experience of the lender as well as their ability to invest funds that will be illiquid.

That way she has a lien on the property and has the ability to legally foreclose if you miss payments and the house will legally be in your name.

But personally, I think you are overestimating your abilities and your savings here.

Knowing the answers to these questions before hand will be one less thing to worry about during the option period and will also give the seller confidence in your ability to close making your offer more desirable than some others2) Know exactly what you're looking for. 

So even elements that don’t appear damaged can be contaminated.

No security deposit to refund- here in NJ the governor signed a bill allowing the tenant to request that it be applied to past due rent during Covid, which she did and we gladly accepted.