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.

.✅ For Long-Term Rentals: Focus on cities with job growth, population increase, and strong rental demand.

Building a sport court will run like $30 grand, but would increase your rental value. a 6bedroom 4 bath house with a sport court, hot tub, fire pit, mini golf, arcade etc. will most likely crush it because it's cool.

Vacancy rates can be highly market-specific and influenced by factors like the local job market, tenant demographics, and property management.

This isn’t about immediate affordability; it’s about creating a sustainable system that gradually reduces costs and increases accessibility through scale and efficiency.Institutionalizing Cultural and Economic ValueSimilar to how pension funds and university endowments operate, this model institutionalizes cultural value.

Low vacancy, tax increase, interest rate increases and insurance increases.

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.

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.

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?

You can likely do this with your savings rate (that will likely increase) and age.