Here, I have seen HOAs take possession and then rent the property out on a month to month basis, using the proceeds to recoup their losses and profit until the 1st lien position forecloses.

That doesn't cure the nonpayment of late fee, so you still have cause for termination.However, if the landlord decides to proceed with termination on that basis alone, the tenant has at minimum 38 days before being evicted (can't give notice earlier than 8 days after due date + you must give 30 days notice) which means there's virtually no chance you're getting a rent check for the next month's rent.

The list is long and it’s all very time consuming.

Here is from FL statues 475.43"All contracts, options, or other devices not based upon a substantial consideration, or that are otherwise employed to permit an unlicensed person to sell, lease, or let real estate, the beneficial title to which has not, in good faith, passed to such party for a substantial consideration, are hereby declared void and ineffective in all cases, suits, or proceedings had or taken under this chapter; however, this section shall not apply to irrevocable gifts, to unconditional contracts to purchase, or to options based upon a substantial consideration actually paid and not subject to any agreements to return or right of return reserve"I will welcome the day when all the frauds and game players are mostly out of business.

So much great information out there and I have just been trying to consume as much as I can.

Disclaimer: This post is for entertainment purposes only.SUPPOSE that I have recently sold a business and am interested investing a portion of the proceeds in either rental properties or flipping.

Or would proceed slower and wait until you've got the initial borrowing speed bumps out of the way?

We are looking at options for proceeds from our house.  

your ability to pull cash and pay down the HELOC will depend on your value of your "investment property," that you're currently buying after you fix it up.If the value is high enough you'll be about to get out a new cash out loan that is high enough to refinance your current outstanding debt plus provide sufficient proceeds to pay down or off the HELOC so that way you can rinse and reuse it again on a new property.As long as you gauged value correctly on the buy side of the investment property you should be fine.As for how DTI is calculated on the HELOC, it depends on who you go to for a loan but typically we'd take the current min monthly interest payment on your current monthly obligation.Some banks had higher hypothetical payment models (assume 1% min monthly payment on the limit of your HELOC) which threw your DTI off, just try to avoid banks like this...

Can he proceed with doing that or can I file against him so a lien cannot be placed?