He left on his own, but when all was said and done, he owed me over $8,000 in unpaid rent and damages to the property.The lesson I learned was to have my processes in place and treat this like a business.

The rate at which you'll be taxed on this recaptured depreciation depends on your income tax bracket, but it can be up to 25%.Now, if you have to sell the STR due to divorce, you'll likely have to deal with depreciation recapture.

Obviously, based on my relationship with the company, I'm not unbiased, but most people here on BiggerPockets know that I value my reputation above all, and when I agreed to join FTF as an advisor a couple years ago, it was because I was very impressed not only with their business model and underwriting guidelines, but with the CEO (Matt Rodak) and the rest of the management team.I have no requirement to invest my own money on the FTF platform; I do that simply because I like the platform, like the deals that are being funded and find the returns to be nearly as good as the private lending I do, but without all the overhead. 

They got into the business to buy homes for themselves.

Blanket answer is it depends.

Duplex or triplex insurance premiums can differ significantly depending on a number of variables, including building condition, coverage levels, and location.

That seems more than just a RE investment: To me, the casino aspect of the investment would require specialized expertise (knowledge and individuals in place to make sure the business is a success) that seems to be a greater risk than the RE side of the deal.

I later heard but never exactly why, that the place was an absolute money pit and the buyer, who was very experienced, regretted buying it big time.It is interesting, but I ALWAYS do at least a bit of research on the prior owners and have found few "hard luck" stories, at least as far as either higher or high priced single fams go, they're by far the same story where the owner makes the financial decision to walk away, mainly due to the insane HELOC's etc they were giving out, like 125% of home's current value back in like 2006, so now they'll owe literally like $750k on a home that IF in great shape would at best fetch $500k, PLUS they trashed or semi-trashed the place, so they'd be really lucky to get $400k as is and often they may be business owners or whatever and have a relationship with a local bank who will then know "the whole story" behind the big hit they take to their credit score and not treat it nearly as harshly as the average Joe, who's practically banned from even entering the bank for years!

The personal relationship tends to mix with the business relationship and this often leads to issues.

Would it matter if I bought this property under my business name?