This assumes that the improvement increases the value of the property, and the points are directly related to those improvements.

If the property is located within the official boundaries of an urban renewal or urban redevelopment district, then you are entitled to be paid for anything at all you do that increases the value of the property.

When preparing for the inevitable costs, always make sur you know the age/condition of your big ticket items.Roof, plumbing, windows, electrical, HVAC, foundation 

There are some lenders that will still work with you, albeit you likely may not get the best terms and conditions.

I was unable to sell it to the rapidly declining market conditions in 2008.

I appreciate crime has increased in the areas recently, but I'd like to think the city will eventually address the issue. 

That said, the risk of wildfires across the state is increasing.

It is more so an annoyance than anything as this money would just be set aside for future purchases but I already am considering the suggestion of @Wayne Smith by increasing late fees and also filing notices earlier in the process. 

While multi-family units can offer higher cash flow, they often come with increased management complexity and tenant turnover, aligning with your goal to minimize hassle.Investment Allocation: With a budget of $300k, diversifying across several SFHs in Raleigh could maximize both cash flow and appreciation potential.

This area seems to be increasing with popularity within the STR market so thought I'd mention to you in case you were interested in other parts of FL.