Can waste a ton of time, money, and effort on this which could be used more effectively evaluating deals, strategies, and markets where you can find returns.Good luck and feel free to connect if you'd like to chat more about it! 

It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

I spend so much time finding the 'right' properties across multiple markets on Zillow before I even evaluate in my buy box.

Ensure you thoroughly evaluate the lease terms and have a strategy to manage potential delays in finding a buyer.Best regards, Stevan

That said it is possible that you need to evaluate your stays and decide if it is worth taking shorter stays or sticking to some longer stays to reduce your time commitment and maximize the revenue for time invested.

You need to know how to analyze property and then systematically evaluate property on a daily or weekly basis to stay on top of the market. 

Are you using a 20-35% down payment when evaluating point 3? 

Are there any particular things to check when evaluating such a deal?

With a 7% interest rate and high HOA fees, the key is evaluating if your skills and investments can generate higher returns elsewhere.

This allows you to see exactly what work is being done and evaluate whether the pricing makes sense.