BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

Some of the condos here have extremely high condo fees. 

@Micah Huffman unless you are going to commit to learning some basics about being a landlord AND are willing to commit at least 2-4 hours each month managing a Property Management Company - it's probably best you sell.Otherwise, it's highly likely you could lose more due to bad tenants and management.

Parking in OB is highly sought after as I'm sure you know.

Many of my clients are high W2 earners who are taking advantage of the "STR loophole." 

However, the success of your project will depend on factors like location, renovation costs, and market timing.Many investors have found great success by focusing on high-demand neighborhoods with strong buyer interest.

Quote from @Joshua Tucker: What specific tax benefits can high net worth individuals receive from building real estate on tribal land?

High probability you won't have cell phone reception if you're close to HH Park.3) Our money could buy something nicer in the Red River Gorge.

Investment Criteria:• “Core” strategy – High-quality properties with minimal renovations or maintenance issues• Stable tenants & cash flow – Long-term leases, steady occupancy• Commercial preference (?)

Here are a few high level thoughts for you as a beginner:-Don't lend in second position-Don't do deals with new investors-Don't experiment with new strategies, even with experiences investors- ie, don't jump in to a first development project with someone just because they've flipped 20 houses.