Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Here's a decent video teaching you how to take marketing photos.

Are there specific market indicators or property traits I should be paying attention to?

I've been wanting to expand out of my market in Iowa, and see that the Winter Haven, Lakeland, Haines City areas are similar to purchase points as my market.

Multifamily is not as volatile as single family because when the real estate markets experience any type of correction, people flee to multifamily residences.

Hi Max, a good rule of thumb is to start with your target market/ideal guest.

Also in my experience it was a waste of time to send letters or any kind of marketing.

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.

I see it every day in my fundings I do in 8 markets. 

You'll likely want someone that can handle A to Z with marketing, pricing, cleaning, maintanence, decor, websites, reviews etc.