I came across this article from Kellogg Insight showing how online sports betting is eating into people’s savings.

(And then any state implications)Given this isn't pennies we're talking about- working with a qualified professional to help mitigate the tax would be your best bet. 

Nationwide, new builds dominate short-term & medium-term rentals, while outdated long-term rentals (LTRs) struggle. Columbus is the perfect case study:
Most investment properties sold here were built in 1900-1950...

A year ago, my taxes were pretty straightforward—just W-2 income and some Airbnb earnings from my place.

Quote from @Heidi Johnson: Quote from @Brian Van Pelt: Quickbooks is straight forward and does not require an 85 Doller version.

My goal is to place tenants soon and then move on to my next investment.While it sounds straightforward to rinse and repeat, now that I have this property, I'm wondering what my next steps should be.

Contract I have in my mind are pretty straight forward with basic things like scope of work, timeline, price etc. 

Any concerns with doing this rather than a straightforward sale and having them handle trust steps after the sale and without our participation?

The process is very straight forward if you have your team in place. 

If you plan to hire a PM they should take care of it for you - if not it seems fairly straight forward.