Currently speaking with a local realtor about the STR zoning issues, insurance issues, and current/future market in Florida. 2025 should be a good time to look for a property there. 1.

And typically long term rentals don't make it easy to include property management fees into the numbers and have them still work well.I would consider looking into STR type areas where you can avoid the risk of property damages (str and pm insurance covers almost everything that they might damage) and evictions/collections.   

Take AirBnB as an example: no one previously thought that a mass market existed for homeowners to let strangers in their homes, or for strangers to rent their space hotel-style.

Currently I have a regular primary homeowner insurance policy on the house as it was our primary home for the past year.

This also removes the FHA’s mortgage insurance premium (MIP) requirement, reducing monthly expenses.Owner-Occupied Financing: If your next property will also be owner-occupied (e.g., a duplex or multifamily), you may qualify for a conventional loan with as little as 3%-5% down.HELOC or Cash-Out Refinance: Use the equity you’ve built in your current property to secure a Home Equity Line of Credit (HELOC) or cash-out refinance.

For a first property, buying in your name with solid landlord insurance is the good starting point.

The insurance quote is $1476/year, deductible $2500, 300k liability. 

We don't have the Midwest weather, high property tax, old homes, high insurance, high maintenance, or state income tax.

Its generally retail medical operators, so we include things like the market dynamics for our use and why statistically the market and location of the site will be viable form a business case standpoint, and speak to how the startup has enlisted the help of an EMR or other such consultant to help in their general rampup and ability to bill/get insurance contracts.  

Sadly, the biggest thing is stressing that it's not section 8 housing as that seems to be the boogeyman for any homeowner.