I was just using a standard 30 year conventional mortgage to analyze the expenses but would like to find a way to analyze it with hard money.

Leverage your cash by using a Hard or Private Money Lender (Other Peoples Money) for the initial purchase (and rehab if possible). 

I recently acquired $100k HELOC.

My question is do I have to transfer funds to my checking/ savings account and let it "season" for 60 days before using it for down payment/closing costs for the purpose of getting a...

I am not using a hard money lender.

My vision is to slowly build a large portfolio, mostly using a buy and hold strategy, to create passive income for myself and future family. 

But using a licensed mortgage loan originator gets you past zero but there's no case law how many you can do when you DO use a LMLO.  

Using a trusted inspector is then even more important.  

Otherwise the cheap option is using a website online with the attorney going back and forth answering your basic questions.You might could see an attorney local  in person for 200 to 300 depending on rates for the area and bring all your documentation.

We feel that we are getting better returns there using a buy, rehab and sell with owner financing.  

An LLC could solve quite a bit of this but he already has enough on his plate and really neither of us want to deal with an LLC on top of all this...So...We would like to take the rent funds in the name of the trust in a bank account and draft checks etc for the building as well.My question is how to set up a bank account for a land trust and is anyone using a bank familiar with land trusts?