I figured it would be a gamble but with the seller still receiving monthly cash flow, I think that maybe it would be intriguing.  

Need I mention gambling is legal in Ohio.

I believe Dauphin Island also suffers from the eyesore of all the offshore oil rigs that are visible. 

Do I gamble my last dime on a single-family cash cow, or do I roll the dice on a flip and hope Lady Luck is on my side?

I offshore my property management to virtual assistants at a fraction of the cost:https://www.biggerpockets.com/forums/530-short-term-and-vaca...

If you really want the property and don't mind a small gamble put down an amount of earnest money that you will not be upset to lose and that if you were in the seller's shoes would make you feel OK about taking the property off the market for 60 days and make it non-refundable to be conveyed to Seller upon offer acceptance. 

I had a few appraisals come back from Akron/Clv markets and had the appraiser comment that it is a "down market".If you are targeting the 50k purchases with the 20k rehab and then hopping to refi out afterward you are taking a gamble because if you do not get the 100k value after the rehab you can get stuck in the project or be forced to take a mortgage with a terrible rate.Keep your purchases 80k and up and try to make sure your project costs are over 100k on everything so you can be pretty confident that you'll get the 100k value afterward.

However, it’s a gamble.

Tenants are a gamble and so is court but you have a 5 year tenant that paid during covid when courts were closed so I’d give that some credit.  

You have got to be net negative overall on your real estate syndication investments --- are you continuing to gamble with your money in this market?