Because in reality, as soon as they exercise the option, I can redeploy that capital into another under valued asset and build wealth quicker.  

Hello Evan, I have helped a number of Bigger Pockets investors build their portfolios in Syracuse and surrounding areas.

Hi David, If building long-term equity and scaling quickly are priorities, then option 2 aligns better for you. 

Does this matter if you're not optimizing for building a ton of wealth to pass onto kids? 

I’ve done a couple of fix and flips but I’m looking to build a rental portfolio.

However, if you're a W2 high income earner or business owner, I can't imagine it makes any sense to flip houses, mail mass post cards, wholesale, or build lead gen websites with the value of your time being better spent other places (such as learning about real estate and increasing your income through proven means), such as at your 9-5pm or growing your business, and your real estate is a long term process and you don't need "home run" deals to qualify or make it work.

I leveraged my owned land to build my personal home.

If you have the sellers, the buyers will start reaching out - it likely wont work for some of them and then you can ask what they are looking for and build relationships that way.

If any one can recommend a good REI focused lawyer or a building engineer to do a building survey then please let me know! 

Along with your list, consider building a local team in each market to make managing your STR easier.