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?

They will evaluate the property, eventual costs with repairs, etc - depending on the service you asks and their fees are about 250 EUR per report.

We're also able to evaluate our rates, and keep pace with inflation, on a monthly and quarterly basis because of shorter term leases.

Like seriously, with as much due respect as I can provide to you in this situation, you guys need to evaluate what you actually do instead of what you think you’re doing.

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.

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

Since you are new to the market, you can look at what the top rent pulls look like and cater accordingly on the design.You always want to build relationships with contractors, but that takes time and you always need a solid bench, just like in basketball because some days your starting plumber just doesn't show up and you need to bring in the backup.The rates are the rates and they aren't going way down soon so it's just part of a different metric to evaluate in your new market.Good luck!

This includes trips to properties for evaluations, trips to Home Depot, etc. 

My best appreciating properties have appreciated over $10k/month over the hold period.the best investors evaluate the risk associated with return.  

Hi Rene,I typically focus on cap rates rather than just cash flow numbers when evaluating properties.