If yes, then I would definitely do it.

We built our personal home from dirt up and while it definitely can be more challenging, you will capture additional value vs buying new if it is done correctly. 

Definitely do-able, but good deals good scooped up quickly. 

We are definitely in a “may you live in interesting times” time.

Definitely I will do. 

Overall it definitely depends on what your goals are with real estate investing, I'd be happy to get on a call to discuss with you!

I sincerely appreciate the advice, I will definitely try to find some multi-family investment brokerages in my area. 

I don't see it outside of something like that but maybe I am missing something Although Whitefish does have tight zoning and regulations, there are definitely areas that allow STR.  

Definitely one of their advantages is that (...assuming you choose well) you can hire someone who will avoid the rookie mistakes so many new investors make when owning property on their own...and has years more of experience and expertise than you could ever acquire.Best of luck to you.

I had my suspicions about the neighbors across the alley and this situation definitely locked it in.