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Honestly you really need to work with an insurance agent to see if they’re gonna be there for you when something happens so reviews are key.Same thing with a realtor.

https://www.biggerpockets.com/users/ZacharyCole/referenceshttps://www.biggerpockets.com/forums/92/topics/518583-feedback-on-renttoretirement-and-zach-lemasterhttps://www.biggerpockets.com/forums/92/topics/765347-rent-to-retirement-reviewhttps://www.biggerpockets.com/forums/92/topics/808479-rent-to-retirement-experienceshttps://www.biggerpockets.com/forums/12/topics/533693-anyone-worked-with-renttoretirement-turnkeyhttps://www.biggerpockets.com/forums/92/topics/581730-rent-to-retirement-zachhttps://www.biggerpockets.com/forums/48/topics/874096-reviews-on-r2r-and-nch?

I'm not an attorney nor do I feel like you need them as much as people think but in this case, please invest a few hundred bucks into a professional contract that is reviewed by a real estate attorney in your state.

So contact everyone :)One of my recommendations would be to contact the source who would review the work at the City of Chicago.

Of the scenarios you list only 1 and 3 make sense to review. 

I'm sure most taxpayers can find a way to justify this and it's probably near impossible for the IRS to determine if every single taxpayer who takes a retirement distribution was adversely affected by COVID19..... nonetheless, something to keep in mind in case your distribution is reviewed.

I will take a look or review how I am coming across to people next time.

Its a small loan, so I'd imagine fees are high but...My apologies, I just reviewed with the lender and the major fees are:$2,850 origination charges$1,100 underwriting fee$1,949 transfer taxes$2,310 property taxes and homeowners insurance$900 homeowners insurance premiumTotal Loan Costs (A+B+C): $6,220Total Other Costs (E+F+G+H): $6,169My FICO is 714

Consider going back to book ‘Rental Property Investing’ and review the chapter on the Application Process.