There are plenty of other markets around the country that are just as fun, but don't come with the ridiculous premium.

Planning should be like that.At the moment, depending on where you operate, inventory for updated homes tends to be in short supply, so it almost doesn't matter when you list.

Some HOAs may not allow rentals or short term rentals. 

Life is too short to chase the rent.

@Mike StadelThere's two ways to do it depending on the renovations necessary:- If it's a short term deal, the investors can wire the full amount to the title company, who then cuts any excess checks made out to both parties.- If it's a longer term deal the investors could wire a portion of the capital (enough to acquire) to the title company to acquire the property.

In short, my long-term plan is to begin investing in SFH (much lower barriers to entry) or small MFH (Duplex, TriPlex, Etc) to raise capital and build my resume with the goal in mind of getting into larger MFH/Commercial properties as quickly as I can. 

(1) That's highly unusual, unless she is short on equity.

Don't look for short cuts - do your full due diligence.

I think the best answer to your question is going to have to boil down to your own goals - both short and long term.  

I found a property that I am very interested in, namely for a personal property but can be used as a short term rental as it is in a popular vacation destination.