@Harsh GuptaIf your main goal is the tax benefit from accelerated depreciation, start by confirming the STR strategy with a CPA who understands material-participation rules, since year-one setup drives the outcome.

At $1,200–$1,800/month in carrying costs (hard money interest, insurance, utilities), that's real money.

Due Diligence & Feasibility (1–2 months)  Start here before you control the land.  

As for the investment, I'm looking to reduce my overall living expenses:Previous Rent Downtown: -$1000/moCurrent Mortgage + Utilities: -$3000/moWhen Vacancies are Filled: -$600/mo (including Utilities, and saving for Vacancy 5%, Repair/Capex 5%, Property Management 8%) Because I'm Self-Managing: -$300/moI'll live here for a year to satisfy FHA requirements, then find my next property.

I can't wait to start meeting everybody

Currently, I am in my 20s, in between jobs, but I have a nice nest egg started with $100k+ invested in the stock market.

Before considering debt service, investors have utilities, taxes, insurance, repairs, maintenance, advertising, HOA fees, and so on. 

We are not real estate professionals.1) How would you handle the classification of the property in the 2023 tax year and would you utilize a STR depreciation strategy?

Many house hackers utilize owner occupied financing programs such as FHA or low down payment conventional loans, which can allow you to purchase a property with a relatively small down payment while still preserving capital for reserves, repairs, and future investments. 

I'm starting out about to do my first flip. how can I avoid as much taxes a possible when selling?