For context, we have been running a successful airbnb for 6+ months cash flowing close to $750/month.

For investors, multi-family properties are great for cash flow, and local networking is key.

You'll need to provide more info on the current financials of the asset you are hoping to buy to substantiate the loan amount and purchase price.

I recently flipped my first property and it was a cash purchase.

Which I currently still hold, and cash flow decently.

I was able to get comps from a friend of mine who’s a real estate agent, but how do I go about finding exactly how much work needs to be done to the home in terms of a dollar amount?

With the additional cash coming in maybe the next journey for you is figuring out how to diversify in another asset?

This is a single-family home in a commercial and multifamily zone, so I believe that if the right investor obtained this property, it could be acquired at a higher price due to its potential for significantly higher cash flow.I'm wondering if I can increase my asking price because of the property's zoning potential.

Should we sell the Red Lodge house and pay cash for another rental, albeit in a lesser market? 

In other words, a wholesaler needs to find a deal where they can get the property under contract for an amount that is low enough that they can not only cut themselves in on the deal (assignment fee, etc), but also pitch it to an investor who sees enough profit in the deal to be worth it to buy it from the wholesaler.