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.

So eventually this negative cash flow property becomes cash flow positive and pays for itself including property taxes, hoa, mortgage etc.Trying to calculate how bad is my investment here or should i sell out if there is appreciation 

When you are creating notes from the start with the intent to sale, you can also consider a 1st/2nd structure that can help you achieve similar results as a partial but start getting cash flow sooner. 

But if your goal is to leave your day job soon, multi family will offer more cash flow typically.

In turn they provide me with a steady flow of off market properties.

Hi there, if you're open to holding onto the property, converting it into an Airbnb or short-term rental could significantly increase your cash flow, especially with the current demand for rental properties.

We have invested in mobile home and multi-family syndications, and we want to diversify into a different segment with good cash flow and some growth opportunities.

Its not as easy but once you are up in running you are building a brand, equity in your business, and also constant flow of leads.

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.Here's a guide that teaches you how to analyze a property.https://www.biggerpockets.com/blog/rental-property-cash-flow...Finding deal that cash flow is the easy part.

Even the funding alone is easier since you now have a cash flowing property that can help you fund your seed money faster.