In my personal opinion, I feel it's dangerous; as you are dealing with sensitive homeowners.

This incident should serve as a reminder to us all - no matter which industry we're working in - to take extra care when dealing with sensitive matters.

I would rather see you find a cheap rental locally and cut  your teeth there.  

However, I asked the management company to do a full checkup of the property and provide pictures, which they didn't and I kept pulling teeth asking about the status.  

Trying to get money from an aging and infermed senior citizen is like pulling hens teeth.

As a landlord i don't want to have the responsibility to protect sensitive financial data.

Rents haven't been raised more than $25 in the past 8 years but seems like there's some price sensitivity with tenants in this area because a few have bailed when there was a small price increase.

But, in Ohio...Business is very sensitive to location traffic count issues.

If you can overcome these challenges, then I say go for it:-How will you navigate time sensitive details during the day?

This could include outlining the terms of the leaseback agreement, establishing the purchase price and any financing arrangements, and addressing any other considerations related to the property's subdivide potential or future development plans.Ultimately, the key is to approach the situation with transparency, sensitivity, and a focus on finding a mutually beneficial solution for both you and the homeowner.