I am not sure how Penfed first claimed that I could do HELOCs on investment properties and now the processor is saying I can't because I can't file the Homestead exemption.

Once you own the property they are now yours....and you will claim ownership, or your LLC, or your OWN trust (if you choose to).  

I see a lot of people making WAY more and claiming they did it in a 1-5 years.

It is completely appropriate and will actually be invisible to the IRS because if the LLC is truly disregarded the property will still be reported on your personal tax return where it always has.A simple corrective quit claim deed is all that's needed.  

Florida’s state level regs are a whole different animal to deal with as well and I can’t claim to be an expert on those (I specialize in every other Gulf state and the Great Plains).To make things worse, a judge in AZ just struck down the current interpretation the Army Corps was using to define what wetlands they had jurisdiction over.

If it is via quit claim deed then you are taking title to the property with all liens and encumbrances.

Again, both signed the lease but I’ve been receiving all payments from Jacks account however Jerry claims he paid half deposit to Jack.

That is of the homeless population that didn't want to leave the streets....oh, they take money and anything free, as long as no rules were involved.Another story I remember from Orange County about 5 years ago....the do-gooders took approx 400 homeless and put them in hotels... free food, medical, everything....all they had to do was live 1 month under County rules.

Per the Mortgage Bankers Association, the vast majority of people who claimed forbearance, actually continued to pay their mortgages. 

Obviously you will want to check with legal counsel - but what many investors have done in the past is quit claim the property into a land trust.