I'd make it 1 car and add more heated sq ft higher appraisal. or make it 1.5 and widen downstairs.

I've narrowed down the best return for my money in this market to a 2 bed/2 bath (with top tier amenities) - about 500 total 2/2 listings.I'm finding myself a bit stuck when analyzing why certain properties are making so much higher than the average listings when they seem to have very similar locations, amenities, style, flow of home, beds/# of people they sleep, reviews, number of reviews, etc.

For lending, your rates are going to be higher than if you were to buy under personal name.

My concern is doing the cash out refi on my other rental and causing a new and much higher payment on it that I can't just pay off like a loan.

In the first you have one tenant, 2500/mo revenue and higher costs.

However, short term rentals are much less passive than long term rentals and are essentially a hospitality business, which is in and of itself required a whole additional layer of knowledge and expertise.With regard to your question about private lenders, it’s important to draw a distinction in terminology between “private” and “hard money.”

Quote from @Saquan Johnson: I would reach out to local rehabbers in that area and also higher-producing agents to get this info.

At the higher PV, you have $5k more in PV and equity).Your CF is around $20k/year, which sounds great, except when you introduce the equity into the discussion. 

Others do this at a much higher level.

Are you two seeing LTVs higher than 80% on that front?