You should have a good idea of every expense you have in your primary home, then add the STR specific:  (These are rough estimate numbers, depending on various factors)STR insurance - a special insurance that covers both the property and your liability, could be $2~4k in areas without natural disasters, could be more than $10k in some other areas.cleaning fee - approx. $50 per bedroom, so a 4-bedroom house will cost you about $150~200consumables - bathroom supplies, kitchen supplies, beverage supplies: $20~30 per week, depending on how much you providewear and tear - towels, linen, kitchen utensils, some furniture: $1000~2000 per yearRepairs/replacement for things that guests break or steal:  $1000~2000 per yearAlso, if your personal use is less than 14 days a year, the entire property's expense is deductible against STR income, but if you use more than 14 days, then you will have to calculate the proportion of how many days it's rented out vs how many days you or your family uses. 

I am experiencing similar issues with time of year being the main culprit.

But there are bunch of factors to consider there. 

This factoring includes the presence of competent contractors who can limit unforeseen surprises and costs.Myth 2: They're Too Risky to Invest InThere is risk in any investment; however, distressed properties are not inherently riskier than any other real estate investment.

Having all Section 8 tenants may cause you to have a higher cap rate on your exit due to a higher headache factor surrounding Section 8.

You clearly have factored this in already.

I mainly am curious how people have raised capital for their first properties. 

I am mainly in the West Palm Beach area.  

Of course, every owner's situation is unique and factors like the legal entity involved, purchase date, adequate passive income that can be offset with the cost segregation study, etc., will need to be considered.

But that is calculated after expenses and depreciation is factored in.