Nowadays many vacation homes are priced as STR businesses with profits baked into the price (with future guests expecting instagram furnishings).  

Define roles, financial contributions, profit-sharing, and responsibilities in a detailed agreement.

However, we also recognize the time value of money, so while it might pencil out to turn a profit, but we get an immediate payback versus a six to nine month holding time, it might make more sense to sell them both as bare land.  

Quote from @Isadore Nelson: 180k + 40k, sold for a 'profit' at 218k? 

Do you need an S-Corp depends on your overall tax situation and profit you are expecting form this flip.This post does not create a CPA-Client relationship.

ST rentals are much more profitable and command cash flows are often higher than in the US if you buy the right property in the right market.As an international investor, I find Ladislas Maurice interesting but there are different types of international investors and most international investors I know wouldn't go through the hassle of what he does for the kind of returns that he gets.

Educate the land owner on the potential profit run the numbers and go over the basic proxy and blue prints.Make sure you have a seasoned and qualified Builder/GC because they can be a deal killer with wasted time and inflated material and extended completion dates.

If i lived in San Jose, the first RE investment that i would consider is a local property with an ADU that had distribution on the lot that would allow a profitable lot split.   

A tidy profit, plus confidence to tackle the next project solo.On the topic of self-directed IRAs: While they’re fantastic for gaining experience and diversifying into real estate over time, they can feel restrictive if your main goal is scaling quickly.Here’s what I’d focus on:Using Equity Wisely: A HELOC or cash-out refinance could unlock funds to pursue a flip or duplex without touching your 401(k).Partnering Smartly: Your realtor friend sounds like a great resource.

Overall, it's been pretty profitable.