I'm pretty new to the game and would love to get some advice from more experienced investors here!

It seems we are facing a similar problem; real estate is not just a numbers game, which is contrary to the thinking of most investors.

Without factoring in tax benefits and principal pay down, you're $1800 ahead of the game by house hacking.

Glad you enjoyed even if your end game is different. 

Quote from @Sean Quinn: My new favorite is in my signature. :)The best book I've read is "The Unofficial Guide to Real Estate Investing" by Spencer Strauss.

I currently house hack in Chicago, however, going from that to STRs where I cannot self manage is a different ball game and just wanting to pick peoples brains who are doing what I'm interested in doing.  

Stessa is a great option, but Baselane is my current personal favorite, partly because it doesn't require that you use a special bank account for rent collection like Stessa does. 

The Pacific Northwest is competitive, so leveraging those connections can be a game-changer.Second, when analyzing deals, ensure you’re building a framework to assess not just the property’s performance today but its future potential.

I've seen some well-known syndicators brag about having "skin in the game" when the truth is they invest $100,000 in $25 million deal but take home $250,000 or more in fees.

It's amazing to see old properties get renovated into something beautiful again - It's one of my favorite things about being a Chicago general contractor!