I would absolutely take tax savings today over tax savings tomorrow.Beyond step up basis, 1031 exchanges or other tax defrayment strategies, you can gain compounded annual benefit by saving taxes today.

I have written before on Bigger Pockets extensively about Tax Sales, so I won't repeat here all the wild, almost unbeliveable properties on the third picked over Tax Sale.

So, Option 2 appears to be a "Roundabout" transaction for the benefit of the Co-Trustees -- not allowed.Option 1 is clearly allowed although not desirable from the tax perspective.Another option, Option 3, would as you noted be the sequential distribution of Property 1 over Tax Years 2-4 thereby  reducing the Ordinary income tax burden by 1/3 each year.

If so, it would seem that banks would prefer investors buy HOA liens over tax liens because at least with an HOA lien, they still have a means to get their money back in due course.

Meet a cpa to go over tax strategies. 

Or...would you rather think about only the money and not have to over-tax your brain by having to do a little more thinking.

More than likely you will have left over tax money to roll over onto other properties that you are invested in. 

Was just going over tax properties at Thanksgiving with our two nurse nieces.  

Account Closed  Good stuff there.I do think we're in for a rocky road here in Illinois given how big a hole the govt is in and how overtaxed we already are (property taxes in some of the towns I'm in down here are 3.5 to 4.5% - and thats actual rate not the 3times multiplier so the rates are 12 to 14 in kankakee and will county towns).I've questioned what the rising rates are going to do.

Their electric grid is already overtaxed before they try to force everyone to buy electric cars.