Follow new listings closely and be definitive in scheduling tours and making offers.

Watch it for a while, track listings, see what sells and what doesnt, what areas move quickly, etc.

.#10 CONTRACT - make sure what you are doing STR is listed in the contract - typically in the addendum section.   

I've seen a lot of talk about house hacking and while I believe that I understand the list of it, I'm just not confident to start.

After 35 years I’ve developed a healthy respect for this business from the school of hard knocks.The day I’ve discovered this business is easy or simple will be a good day to retire.

Charming, smaller coastal towns with a slower pace of life, natural amenities, seclusion and semi-self sustainability are high on the wish list of many high level clients and investors. 

I've talked to two local agents about possible price points to list at, but it almost seems like they are pulling numbers out of a hat.

By my estimates, pricelabs cost me approx $25K last year in lost revenue for some of the same reasons you've listed in your post.

Luckily the property hasn’t gone down in value so the lender lists it for $400k and gets it.

I don't know any investors who purchase without an inspection, though I hear about this mythical "no inspector" purchaser from time to time, by way of the rumor mill or pompous listing agent.