Here's my take on the decision:First, let’s look at the pros and cons of paying off your current short-term rental (STR):Paying Off Your STRPros:-You Eliminates your largest fixed expense (the mortgage), which increases your cash flow significantly.

We plan to remove them all to protect from tax increases on our current primary, but I am afraid that now that the other properties won't have homesteads, we may see skyrocketing tax bills and it will eat into already small cash flow from rental income.Does anyone have advice for how to handle this situation other than just increasing rent?

Ithaca, 10.8% YoY housing prices increase.

Our auto coverage is now at an increased level so if this happened today it likely would not result in any involvement of the umbrella policy. 

However, if you're a W2 high income earner or business owner, I can't imagine it makes any sense to flip houses, mail mass post cards, wholesale, or build lead gen websites with the value of your time being better spent other places (such as learning about real estate and increasing your income through proven means), such as at your 9-5pm or growing your business, and your real estate is a long term process and you don't need "home run" deals to qualify or make it work.

Slight Update: After speaking with more BP members, I’m increasingly leaning toward making my first purchase in New York—a 4-unit rental property where I’d be my own landlord.

They may also require US credit history, although there are a handful that will not require a US credit report for an increased rate/ reduction in LTV. 

Lastly, if you’re currently taking a homestead exemption on property taxes, once that drops off (if you’re currently taking chose to transfer the exemption to your new home) your property taxes will likely increase $1k-$2k thus increasing your monthly mortgage.

They may have been introduced to wholesaling as a low-barrier entry into real estate and never considered licensing as a viable option.Why Getting Licensed Could Be Beneficial:Access to MLS: Licensed agents can access MLS listings, making it easier to find deals and run comps.Credibility: Being licensed can increase trust and credibility with sellers and buyers.Expanded Opportunities: As you mentioned, having a license opens up the option to list properties traditionally when wholesaling isn’t the best fit.Legal Clarity: Licensing helps clarify what you can and can’t do, reducing the risk of running into legal issues that plague unlicensed wholesalers.It’s a balancing act, but for many serious operators, getting licensed seems like a logical step to expand opportunities and ensure compliance.

Schools are solid, demand is high, and I think that you'll see an increase in housing prices in the future.