I like the Ocala market but not sure if this is a good opportunity and if the Ocala market is a good one for REI.

Given that he's got a long history in business but is struggling to cover $30k in Op-ex and marketing spend, my guess is that this is either not very well managed or is in distress.

My worry is that the property might fall into probate or tax auction once he passes and someone who knows someone will get the deal under contract before it reaches public offering.There is a real estate agent in the area that gets about 85% of all the listings in the micro-market, so she is farming these properties constantly. 

It may be common in your market.

In any market, you need to analyze median income, and crime, and that will help predict where you will have more challenges collecting rent.Every city has their challenges with vacancy.

Hello everyone, With deciding to start in real estate, my main goal is to create enough equity in the properties I obtain to build a house and buy land  (10-12) years down the line.Though the market always changes, I figured with investing into highly appreciating markets now, the properties I buy will accumulate the equity needed to be able to sell in the future which in turn will lead to the income needed to build and buy land. 

Once you have that, you can look at what similar properties in your market are doing for design.

We backed out of that deal because there was a freeze that hit Texas market, and that freeze caused a bunch of plumbing issues.

On the first occasion, I leveraged it as an opportunity to move the tenants along, complete some rehab, rerent at market...

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.