.- Can't see a Senior-Only complex allowing Short-Term-Rentals (STR).If so, SELL.2) What is the history of Association Fee increases and how well capitalized is the Association for future repairs?

It may make sense for the right purchaser to repair.

The Property Manager usually does light cleaning and repairs between tenants.Recommendations or another way to think about this? 

Here's a list of things to track:- Formal lease application- Formal signed and executed lease specific to your state- Payment history (I recommend using online rent collection like Apartments.com, RentRedi, etc)- Maintenance requests and receipts- Accounting for all rental-related expenses (repairs, utilities, etc) The more you treat it like a business, the more helpful you are to your CPA come tax time. 

Cash Partnership 50/50 on both the purchase and repairs.

Plus, you have to turn the unit over- paint, carpet, etc repairs?

Even if you break even, you will lose money every month it sits vacant, when you need repairs, property management, etc.

However, I didn't lay out what that seller financing offer would look like because I'm really not sure if a deal can be made or how that financing would look.I'm hoping to find a way to get the home owner some money in her pocket if possible, although I need room for an investor to fix the issues and hopefully buy the lot back from the auto repair shop.

The house was flooded to the tune of $70,000 in repairs. 

How much will you spend in repairs on a 1920's house with renters ?