In some cases, after running the numbers, I’ve even faced potential negative returns, causing me to miss out on promising deals here in South Florida.That brings me to my question: I currently own two homes—one is my primary residence, and the other is a rental property.

Now his original property is less cash flow, and is his 2nd is likely negative $500/mo.

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

It's like putting your life into net negative before you are trending enough into financial positive.

Quote from @Nate Sanow: Yes I own two that are near 100 years old and I will tell you they are a pain in the you know what compared to all of my post WW2 properties especially post 1980… layouts are better in the last 50 years and energy efficiency is better and I can keep going… HOWEVER to reply to the other aspect of your question, I’ve found appreciation is better with older properties in areas of the path of progress.

Which of course is actually a negative for participating in speculative madness. 

I'm not sure why not - one of the great parts about real estate investing is that you can build a team around you for aspects you aren't as strong at or simply want to delegate to someone/expert and do the others yourself - look up "Core 4" for example - where you can have an agent, lender, manager, contractor all at once for your investments and can theoretically just let them do all the interactive work

Just remember: most negative reviews are written by problematic tenants.

What aspect of their business, the property managment software or investment management software.

Curious as to whether anyone uses them and has anything negative to say.