In Indiana the clean answer is you do not need a license to lease out and manage your own stuff, but once you start doing sandwich lease option style deals in a way that looks like you are brokering for someone else or getting paid to put deals together, you can drift into the part of the law that says you cannot negotiate leases options or sales for consideration without a license.

One agent advised to sell the condo but 3 considerations make me hesitate: 1) My motivation for holding the condo and renting it out was not the cash flow but steadily building equity while the main ownership costs (mortgage + HOA + property tax + insurance) are fully covered by the rent.

That makes cost segregation even more powerful since those reclassified assets can potentially be fully deducted in year one if you qualify.Key considerations: Land is not depreciable.

Proximity to a nearby course alone does not qualify.Investor considerations:• Attracts a loyal, higher-income demographic• Strong potential for destination travel, group outings, and repeat visitation• Revenue streams extend beyond rooms (green fees, memberships, food & beverage, events)Key risks:• High ongoing maintenance costs for course operations• Seasonality driven by climate and regional demand• Requires professional turf, water management, and course operationsInvestor takeaway:Golf resorts operate as lifestyle assets, not just lodging.

= 20-40k-- Capex (target 1% of capital) = 10k-- TOTAL = 47.5-67.5k- CASH FLOW (YIELD) = 32.5-52.5k (3.25-5.25%)Based on that math, it's considerably better/higher yield to switch to STRs compared to the $15-24k cash flow in my LTR.

Quote from @Johnny Link: @Jason Malabute thanks for calling this out, do you mind going into a bit more detail on some of the key considerations for whether "some or all of that benefit" is taxed upon sale for those of us less familiar?  

However, an important consideration is whether the property was professionally cleaned before the tenant moved in.

The cost difference of $66,804 ($72,750 - $5,946) is far greater than any likely maintenance cost difference.)Additional consideration: You can refinance your loan if/when interest rates drop, but you cannot lower your taxes.ConclusionThe lower interest rate on a new home is attractive, but it's not what matters most.

Your calculations also aren't taking into consideration CapEx, Maintenance, Vacancy, and possibly Property Management. 3.

Becoming a licensed agent when you are old enough would be another consideration although if you actually composed this well written post on your own I suspect you are super bright and would strongly encourage college either first or in conjunction with your RE goals.