I owe $95k on the property and it is worth $150,000.Unit 1 rents for -$550Unit 2 rents for -$650Unit 3 (my unit will rent for -$700-$800)My plan was to move out of this house into a Fourplex, then rent out my current unit- resulting in $800 plus cash flow out of the Triplex.

If there are repairs and work those funds should come from the LLC.If you personally are paying repairs etc out of your own pocket your LLC will owe you Back that $, but if this is not tracked a CPA an attorney will most likely tell you don’t even bother having a LLC as you are commingling funds and the asset protection you is essentially voided. 

He purchased the property in 2004 for $95,000 and currently owes roughly $65,000.

The bond company pays the claim but then they actually go after the tenant to collect what’s owed. 

Having a CA LLC you will have the privilege of paying an additional $800 charge on your CA return, and you may also owe another $800 fee for both the Texas and Wyoming LLCs if your activity rises to a certain minimal level.If any of these entities are multiple member LLCs they may be taxed as partnerships and its my guess you will need some professional assistance for that.

If they only owe $375k then there is no reason/way they could even short sell. 

I'm guessing that interest rates for this would be 3.75 - 4% owing to the cash out part. 

Let's say you bought a place for $150k, paid on it for years and now only owe $100K, and the place is worth $200K now.

And keep in mind, the insurer has perfected title as insured so it's fully performed its obligations, it won't owe you anything else. 

When I divided the price by square from from realtor.com it came down to $504 per square foot-Offer: 300k at 3.75 for 40 years =579k after interest and principal.