A lot of investors are (wisely) wary of condos because condo fees can rise and special assessments can eat up your cashflow.

I personally would approach this with a self assessment.

One street where I owned two properties, I check the assessment records and found that of the 22 houses on the street 20 were owner occupied and my 2 were the only properties that were not owner occupied. 

I would be purchasing with an FHA loan, how do i assess if the deal is worth it?

.- Research the Flipper:Look into the history of the flipper or the company that did the renovations to assess their reputation and track record.Be Skeptical of the Cosmetic: Look beyond the surface-level improvements to understand the true condition of the home.Taking these steps can help ensure that you are making a well-informed decision and investing in a quality home.

A credible lender will be happy to provide them.Experience: Check how long the lender has been in business and their experience with similar projects.Red Flags:Upfront Fees: Be cautious of lenders asking for substantial upfront fees before any services are rendered.Lack of Transparency: If a lender is not transparent about terms, fees, or the loan process, it’s a red flag.Unrealistic Promises: Beware of lenders promising guaranteed approvals without a proper assessment or offering terms that seem too good to be true.Poor Communication: Difficulty in reaching the lender or getting clear answers can indicate potential issues down the line.By conducting thorough research and due diligence, you can confidently choose a reputable hard money lender that meets your needs.

I established a  mgt entity for leases, deposits, income, expenses, but never held any of my dozens of residential rentals in LLCs over my 21 year run.It's just tougher to get good mortgages and insurance. 

@Michael Plaks has a great post on this topic.2 - Assess the value of those tax deductions to you: The value of a deduction depends on (a) whether you're actually able to use it to reduce taxable income and (b) your marginal tax rate.As an STR, assuming the average rental period is 7 days or less, key items to consider are: (a) material participation and (b) avoidance of "excessive" personal use.

This experience highlighted the importance of thorough initial assessments and flexibility in budgeting, reinforcing the need for strategic planning and adaptability in real estate investments.

Presented by Premier Law PLLCAccording to Florida tax regulations, real property without a homestead exemption is eligible for a 10% cap on annual increases in its assessed value for real property tax purposes.