If you engage in an active business such as flipping - UBIT may apply, be sure to speak with knowledgeable CPA to understand the tax liability. 

That could be a great way to find and stay engaged with local investors, realtors and opportunities. http://www.biggerpockets.com/alertsYou can also search for other investors or brokers in those target markets and follow their journey on Bigger Pockets here: https://www.biggerpockets.com/search/usersAnything you can do to build your network in the region will help you find the realtor, and eventually the property, that suits your needs.

That could be a great way to find and stay engaged with local investors, realtors and opportunities. http://www.biggerpockets.com/alertsYou can also search for other investors or brokers in your target markets and follow their journey on Bigger Pockets here: https://www.biggerpockets.com/search/usersBest of luck to you and look forward to following your journey!

is it wise to engage the listing agent directly to draft offers?

That could be a great way to find and stay engaged with local investors, realtors and opportunities. http://www.biggerpockets.com/alertsLooks like you've already made some connections with BP members there in your neighborhood...You can also search for other investors or brokers in in Tacoma / Olympia / JBLM, and follow their journey on Bigger Pockets here: https://www.biggerpockets.com/search/usersBest of luck to you and look forward to following your success on BP!

It also keeps me engaged and motivated.

Corporations and LLCs must engage lawyers for any legal proceedings.I sincerely doubt that your personal umbrella covers your apartment management now, since every personal umbrella policy I've ever had always excluded business pursuits.

Big thing for me on podcasts is you have to be engaging and informative, not too boring, showing character and such.

I'm in NY and insurance companies licensed to operate in NY may not be licensed where you are.Also, I own rentals and engaged in several other businesses, and it's best to know and use an experienced insurance broker in your area, preferably a local one.I once bought a business for someone who had his business in an S Corp., didn't realized when his business get sued, lawyers normally sue the entity and the owner personally as well.

There are a number of purchase/sale/holding costs to look out for, that I compiled into this post here: https://www.biggerpockets.com/blogs/8814/70530-fix-and-flip-project-costs-purchase-sale-and-holdingI see that you're located in South Dakota, so in addition to those costs you'll also need to contend with the Contractor's Excise Tax, which is a 2% tax imposed on "prime" contractors engaged in "realty improvement projects" in South Dakota.