They were living on the main floor, the 2nd level is vacant for a longtime now and their son was living on the 3rd floor rent free. 

We reach several verbal agreements, but they never return a signed AOS with those terms or submit counter offers. 

@Terry N.You likely won't find a free tax estimator online.Tax rates change ALL the time imagine a free software that would have to keep up-to date on all of this.Furthermore, each taxpayer live in different jurisdictions which result in different state tax rates.In general, long-term capital gains at the federal level is normally 0%, 15% or 20%.There is an additional 3.8% net investment income tax if your income is above a certain level.There is no preferential tax treatment for short-term capital gains.You may want to consider reaching out to your accountant discussing what property you plan to sell and he/she may be able to tell you the estimated taxes on the sale.

temptation at the pro level is huge from friends family etc. 

I have several listings now where we are helping our sellers with this issue, and it is not easy even with the experience level I have dealing with tenants. 

Was it detailed books or just high level? I

@Eddie Lunsford I have no idea of your knowledge, experience or skill level.  I

As a matter of fact, you may be able to get some good answers for your area just by interviewing a few prominent mgmnt companies in the area.That aside, maybe try talking to the tenant and meeting them at the "human" level. I

In Austin, you'll need to look at larger down payments to achieve a cash flow positive level. I

It just depends on how much you would like to put down and what your comfort level is.