There are a lot of note buyers out there in the secondary market that like owner generated paper.. if you buy cheap enough you can still do very well with the higher returns those investor expect.I help my land flippers I fund do the same thing even today.. 

Rent out both units to cover the mortgage while we subdivided the land and built properties to sell on the back half of the land.Option #2: 1 year - Same as option 1, however, instead of building more units, sell off the lots to builders.

Thats another tactic;  low ball bidding, then cost increases mid-project.A 3/1 or 3/2 rehab keeping the 3/2 exterior walls but moving interior walls;   Maybe $110k

Also be careful as 2019 was a reassessment year so the coming tax bill may already be higher than 2018 was.For your example, 75% of $187,000 is already lower than the prior taxable value of $154k, landing at $140k. 

Just wondering what others have tried that made you land the deal?

When it comes to taxes, it'll depend on the country.I personally haven't and I won't invest in Asia because you almost never can own the land freehold.

So we have 3 buckets in my mind - SFH sale (basic), developer sale for the size of land (new to me), business sale (home + business).The most value would be in selling home + business I believe but I have no idea how to market/find potential buyers for such a thing.

Rent out both units to cover the mortgage while we subdivided the land and built properties to sell on the back half of the land.Option #2: 1 year - Same as option 1, however, instead of building more units, sell off the lots to builders.

If it was me I'd sell Encinitas take the 1/2 mil tax free, keep the land in Carlsbad and build that dream home, and have a fun project with your mentor's home as a retreat.  

I was thinking I'd buy an acre of land that has city electricy and water available, and pay that off so that it can be used for collateral one house at a time.