@Chris Schwartz I see, because in your example the profit would be 40k non taxable to the seller, the taxes shouldn't be an issue when distributing to family members.

You can't directly do something to allow you to sell the flip, and buy the triplex without paying gains. 

Deal with one of the large accounting/tax companies that have an international network.2.

Rentals generate passive income, so an S-Corp offers no added tax benefit.

When it's sold it will be taxed as capital gains tax and may also have some unrecaptured depreciation which is capped at 25% and  recaptured depreciation as well which can be up to your ordinary income tax rate.

My fiancé and I are currently looking to invest in Fl, and have been looking into tax deed sales. 

They could easily pay 50% two weeks early, then pay the other 50% on the first so they are always on time.

I would for sure keep the association, some associations have an overlay that you have to be paying into NAR as well.

How are you feeling about filing your taxes this year?

We are saving around 50%+ of our income on a yearly basis, while also putting away for retirement and we would both like to get out from under the mortgage on our primary residence sooner rather than later.After plugging in some of our numbers to a spreadsheet to simulate a first lien HELOC it seems to indicate that we would be able to payoff our primary residence in ~10 years while also paying significantly less in interest from a conventional mortgage.