I am not new in RE (Own 2 (condo+townhome) +primary home) and all units are in San Diego and know want to buy something near beach and been in Imperial Beach lot of times love the place :)Any guidance how should i approach?

He intends to use part of it as a down payment for his primary residence, but he wants to use the rest to build something bigger.

If you want to live in those areas anyway, it's very likely that house hacking in those areas will be better than just renting or buying a primary home just to live in.If you need lender referrals, send me a PM and I'll get you connected.

Tax Write Offs: There are certain tax benefit to house hacking because you blend benefits of primary residence with rental income.

The costs for the LLC business will be paid with the primary business card.  

From what I have seen, flipping and STRs are the best way to make deals work here, but the primary objective is appreciation, not cash flow. 

@Adoney Reid are you planning to buy this as a primary residence and house hack or buy as an investment property?

Apparently Chase only allows transfer to LLC's if it's your primary residence?

I could pull a heloc on my existing primary home (in Florida) to purchase the land and use towards the build along with cash (50/50).

I do have a mortgage on what was originally my primary home two years ago.