I’m new to the rental business.

You need to have a solid understanding of the business as a whole.

I would be planning to do some things before actually making an investment.

Shaun Shaun,I am a "specialist" and currently a business owner of a design and drafting company in CT. 

That means creating a clear budget, forecasting cash flow, and maintaining a detailed financial model that tracks both the current and future performance of your portfolio.Tax Optimization & Risk ManagementBeyond financial clarity, strategic tax planning and risk management are essential to safeguard and grow your real estate investments.

I'm planning on doing a str loophole so low priced str won't work well for me 

I plan to consult a tax professional but before wasting anyone's time I would like to ask whether I can technically claim the property as a rental in 2024 even though our first contract started Jan. 1, 2025?

Do they come with subscription plans for maintenance ?

Im only thinking about doing this because I think he wants at least 400k.Does that sound like a smart plan?

For the community development dept, you'll need proper plans (architect), site survey, permits, etc. when you're ready.