But over 95% of the stays there were no problems, and I'm blessed that my LTR tenant has great pride of ownership in our property so he looks out for the property and has even offered to help maintain  parts of the outside of the duplex to ensure my STR guests always have a great overall impression of the property upon arrival.

Maybe you will comment on that too as part of what you're willing to accept to maintain cash flow/performance.

As far as maintaining your books goes, start with an accounting software like Quickbooks.

1) Make sure to get your BBL License and Rental Inspection Completed2) Purchase Umbrella Insurance3) Maintain your property4) Maintain good relationship with your tenants.

However, it's important to keep in mind that there are still considerations to be made for the comfort and convenience of your guests, such as providing access to amenities and ensuring that the space is well-maintained and clean.

Even with a building with free market rents, it would be near impossible to acquire and maintain it on positive cashflow, but it'd be a nice way to write off some taxes on it and slowly accumulate equity + appreciation over the years. good luck!

It always boils down to the main part of the home, and what type of soil was it built on.I have seen 150 year old homes that were in perfect condition and well maintained, these homes usually sat on elevated grounds with good drainage (which limits the movement of the foundation).When a house is built on flat ground and or where clay is present.

You should connect with some CPA's to find out what the cost to file and maintain the LLC will be so you can have an objective look at the pros and cons. 

At minimum, a property should be maintained in same quality/condition as purchased. 

Wanting to maintain a minimalist lifestyle with a smaller space in order to maximize our savings to achieve financial independence.