Looking for advice on STR strategy and markets

[Robert Johnson]

Hey everyone, new investor here. 

I have a clear goal of trying to hit $3k / mo in net cash flow and I have a moderate-to-high risk appetite. After some initial research this has led me to being attracted to STRs.

I've read "Rental Property Investing" and "Short Term Rental, Long Term Wealth" so far this year already. Ideally I'd like to find a property where I have a reasonable chance of not losing my shirt with contingency plans (i.e. retain the ability to use it as a LTR or MTR if STR doesn't work for whatever reason). I have the time and willingness to self-manage remotely. Because this is my first property I'd really love to find something as turnkey as possible and avoid rehabbing.

I'm wondering if I should buy the bnbinnercircle or BP STR BootCamp program first or just get to identifying markets and talking to agents that specialize in STRs to start underwriting properties to estimate cash flow? I have a spreadsheet set up already but the "Short term rental, long term wealth" book didn't go into that much detail in estimating gross annual income. Yes I'll use AirDna and any other tool I can find, but if anyone has a good resource for estimating this I'd super appreciate it. Lastly, I'm looking for some advice on how to narrow down what market I'm looking at. I downloaded the STR Insights 2024 report and am looking through that, but combined with using AirDna's data and asking myself "where would I want to vacation" I'm feeling a bit of analysis paralysis. If it's helpful, I love the outdoors. I surf, I climb, I love the mountains and hiking so any of that feels interesting. Thanks!