Laud area-Cash flow is minimal, $300 a month-Selling now would allow opening up of equity to redeploy in another market with over 2x the cash flow for a new build-New market won't appreciate as much as FL though (not even close)-Current home will likely get hit with higher taxes, insurance etc. in coming year and years to come-Biggest reason to consider just keeping current property?

When I did underwriting, since a portion of the insurance costs and property taxes are collected at closing, I reduced those from the first year of expenses.

Or better, buy a property that is not subject to an HOA.Also, if you are leasing for 6 months or less, you will be subject to the 6% Florida short term rental tax.You may also have city and county additional taxes, business tax receipt, and mandatory inspections for short term rental depending on the jurisdiction where your property is located.

To diversify further and maximize tax-free or tax-efficient retirement income, there are several strategies you can consider.One key option is real estate syndications or private REITs.

Hey, that's a great question and definitely a smart one to ask when you're diving into the details of STR (short-term rental) investments.Let me break this down from both a tax and practical standpoint based on what I’ve seen with clients in similar situations.

You often hear from real estate investors who scaled businesses  attribute their success to great contractor relationships, a realtor who helped identify an underserved housing need, lenders who gave them a chance despite not having a balance sheet, even good attorneys who navigated them through entitlements or perhaps accountants who educated them on tax saving strategies.  

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

.- You mentioned you don't need the money right now, so holding onto the property could provide long-term rental income and potential appreciation.Here’s what you should consider:- **Financing Costs**: If you decide to rent, ensure you factor in all expenses, including mortgage payments, property taxes, insurance, and maintenance.- **Market Conditions**: Check the local rental market to see if $1450 is competitive and if there's a high demand for rentals in your area.- **Long-term Goals**: Think about your long-term investment strategy.

KC is a great long term rental market for low taxes and landlord friendly.

You'll pay capital gains tax on the gain on the sale.