How much will be due in repairs over the next five years? 

Rents were well below market and substantial repairs were needed.

The water leaked through a shared wall into their neighbor's space and repairs are being made.

Many new investors get excited by high cash on cash returns in the midwest and buy rough properties in D areas and they get smoked by property managers, tenants, vacancy, capital expenses, repairs, turnover costs, etc. 

Mostly messaging with guests regarding issues, questions, concerns, as well as coordinating repairs and restocking supplies. 

@Derek BellWhat would the after repair cap rate be with a 362,000 NOI?

Then all you realistically can do is manage bookings, delegate to handymen for repairs and hire cleaning service.

I'm doing the best I can, the bigger house will probably cost more for purchase and repairs. 

:) Its generally a good idea to know the condition of a property or level of expected repairs so you can anticipate those repairs and build them into your bid for the property.

However, if you're set on managing it yourself there's plenty of websites and apps you can utilize for rent collection.Some may or may not include messaging for requests such a repairs or maintenance, but if you're looking for rent collection there's quite a few options on the market that are affordable.