If NY is where you decide to be I would strongly recommend connecting with @Mohammed Rahman he is who I would use. 

I strongly advise you to get your primary residence taken care of FIRST.

If you move to NYC, focus on maximizing your earning potential while investing in affordable out-of-state markets with strong rental demand, like San Antonio or Indianapolis.

Explore off-market deals where competition might be less intense.Don’t get discouraged—success in these markets often comes from building strong connections and thinking creatively about deal sourcing!

Starting your real estate journey with a house hack in Austin is a smart move, especially with its strong rental demand and appreciation potential.

Detroit has a mix of affordability and strong rental demand, with properties under $200k that can cash flow if approached correctly.

Kissimmee remains a strong market due to its proximity to Disney and other attractions.

What I am trying to understand is after Coachella ends, would it still have the strong recurring demand/occupancy for STRs?

Focus on areas with strong rental demand, like Broad Ripple, Fountain Square, or near universities like Butler and IUPUI.Maintenance Costs: Indiana weather can be tough on properties, so budget for seasonal maintenance like snow removal and HVAC servicing.Additional AdviceKeep an Emergency Fund: Unexpected repairs or vacancies can arise, so having 3-6 months of expenses saved will help you weather any surprises.Build a Reliable Team: I have lists of contractors, handymen, cleaners and property managers if you'd like me to send.Good luck with your property and future expansion!

Look for a team with a strong track record in managing rentals like yours, especially in your target area.