In short, having all the conversations and commitments in strategy, setting up LLC and all the fun docs of who's doing what, and I'd suggest even getting initial funding into account for at least EM. 

I’m new to the real estate game.

We also just purchased a house in Oliver, WI that we plan to run as a short-term rental.

@Matt Schreiberi think the short answer is... no.but... a lot of inputs missing - which market? 

It's a short term lease.

The short answer is, Pricelabs users don't fully trust Pricelabs to set the correct rates.

A small multifamily property is a smart choice for a first investment—it offers a great balance of income potential and manageable scale for someone new to the space.Don’t worry about being ambitious; it’s clear you’ve done your homework, and you’re already ahead of the game by setting a clear goal.

Address Your Financial ProfileBridge the Revenue Gap: Highlight your equity in the duplex and use your sale proceeds to demonstrate “skin in the game.”Partner to Compensate Experience: A financially strong and experienced partner can help offset your limited track record.Focus on the Land Deal: Secure the land at a good price, as it’s a crucial step in gaining credibility and attracting partners.Final ThoughtsYou’re entering an exciting and impactful space in real estate development.

Own and just keep it as a rental longterm/short term rental?

I'd focus on deciding what you want to do (flip-high risk, but potentially high return...or large loss; short term rental-more work, but higher return than long term rental; long term rental-less work than the other two, but lower return).Once you've decided which you want to do, then focus on getting the best house to meet your goal.