Don't forget to add an adviser to your team to work with your CPA/tax professional to maximize the tax benefits available on each and every project.

CA for instance has hundreds of thousands of paper lots that were created between about 1900 and 1935. these paper lots get sold at tax sale all the time and its where a lot of the land geek type of players toil. 

For example, there is one poster here who's business offers a note fund set up as a c-corp rather than an LLC in order to offer dividends that are more tax friendly for IRA accounts (at least that is how I interpreted it).

Due to taxes, the up and down nature of stocks and also out of a desire to actually own something real and tangible, I decided to invest in real estate.

At the state level a law was proposed to place additional 15% tax (on top of local occupancy tax) on STRs.  

IRS guidelines would require you to seek out a tax professional but i believe you are taxed on gifts above $14k.

Complicating this issue is the need to do a 10-31 due to stepped up value/capital gains tax on half of the land.  

The requirement to defer all tax is simply to purchase at least as much as your net sale (in your case 50% of the net sale of the entire property). 

What would be the best way to do this for tax purposes, liability, and breaks? 

Rental property owners, did you know you can deduct expenses like mortgage interest, property tax, operating expenses, depreciation, and repairs?