When you do "short-term," you're actually considered an "active business" subject to self-employment tax as well as your personal income.When doing wholesale (for example) through an S-Corp, you may treat part of your net gain as a distribution wich is not subject to self-employment tax.

Unlike passive rental income, the income from an active trade or business is subject to self employment tax (a nasty 15% tax commonly referred to a "social security and medicare" by working folks).

in Non disclosure states your tax records will show purchase price 10 bucks.. this is how they work in Mississippi.. so if its off market there is no way to know what someone paid for it.. the assessor assess it by local values for tax purposes.In CA in the good ole days it was common for developers to pay more stamp duty.. as you could back into sales price by figuring out the transfer tax as it was based on a % of the sales price.. so developers would pay more on purpose to give the illusion they paid more than they really did..  

If so, you buy in Teddy LLC, and then sell to Teddy individually, the spread will be taxable ordinary income plus self employment tax, as the profit passes thru the LLC to you, unless the LLC is taxed as a Sub S.

I really know nothing about the rental market in Sao Paulo, Brasil, so I'd have to do my research. 

I'm a new member from sao Paulo, Brazil.

Now I am in the process of searching for a CPA/tax preparer to help me minimize the impact of the depreciation tax as well as prepare my company's annual tax work.

@Val BerechetAt its simplest, you either pay the capital gains tax as a percentage of sales (25%) or net profit (30 or 35% - check for the latest figures with your tax advisor.In most situations, the net profit route will be the most advantageous just based on those percentages.

@Nathan Becker one thing to consider specifically in TN is the F and E tax as it relates to LLCs.

If you rent out your current home and don't sell within 3 years, you lose the homeowner exemption on capital gains tax.