But these are VERY rare occurances and one can spend years unsuccessfully attempting to conclude this type of transaction. 

Are lenders going to care about amount of experience with this type of deal in terms of preparing a fleshed out model, or is it similar to retail in the sense that much of the process is managed?

I never call it a "cash offer" (it's not), but don't complicate it with all the extra amendments and contingencies.If the buyer gets the property under contract and has to fill out an addendum that asks for financing type, I will always indicate that the purchase is financed if the buyer is using private/hard money.And I'll always include however much time is needed for financing approval into the due diligence period, so there is only one contingency in the contract, not multiple.Doing it this way allow us to be completely honest and transparent, but still give us the best chance of getting the property under contract.

I also do a meetup every Thursday but we are currently doing it virtually and we actually contact agents that have properties for sale so it's an 'active lead gen' type of meet up. 

Hell wit the type of money you have access to I'd almost rather see you become a private money lender for another experienced flipper, who has made the mistakes, has a proven track record, has the dealflow, and the crews, and will pay you a handsome return on your money. 

Coachella Valley is quite complicated because a number of areas have some type of prohibition on STRs. 

What made you interested in investing in this type of deal?

Types of properties needed, regulations, etc. 

Your property really has to suit your guest type, stand out against the competition and be priced right.

I'm sure all I need is a experience title company or attorney who actually handled this type of deal before.I'll call Friends Title and sure will mention you referred me.