If you have any doubts....here's the exact verbiage from Fannie Mae:B3-4.3-15, Borrowed Funds Secured by an Asset IntroductionThis topic contains information on borrowed funds secured by an asset, including:• Borrowed Funds Secured by an Asset• Secured Loans as Debt• Reducing the Asset by the Amount Borrowed• Documentation RequirementsBorrowed Funds Secured by an AssetBorrowed funds secured by an asset are an acceptable source of funds for the down payment, closing costs, and reserves, since borrowed funds secured by an asset represent a return of equity.Assets that may be used to secure funds include automobiles, artwork, collectibles, real estate, or financial assets, such as savings accounts, certificates of deposit, stocks, bonds, and 401(k) accounts.Secured Loans as DebtWhen qualifying the borrower, the lender must consider monthly payments for secured loans as a debt.If a secured loan does not require monthly payments, the lender must calculate an equivalent amount and consider that amount as a recurring debt.When loans are secured by the borrower’s financial assets, monthly payments for the loan do not have to be considered as long-term debt.Reducing the Asset by the Amount BorrowedIf the borrower uses the same financial asset as part of his or her financial reserves, the lender must reduce the value of the asset by the amount of proceeds and related fees for the secured loan.Documentation RequirementsThe lender must document the following:• the terms of the secured loan,• evidence that the party providing the secured loan is not a party to the sale, and• evidence that the funds have been transferred to the borrower

Screen your tenants well, try to find a responsible one who will be willing to "manage" the property in exchange for reduced rent and take as much security as the law allows and you will be OK. 

Is there any assurance to help ease the stress of making sure someone rents the unit out?

Access to international buyers is one thing I stressed when talking to realtors and the one I chose originally told me that their firm does have international exposure but that turned out not to be anything past putting my property on their usual list of websites.

Or you may decide to reduce your risk by having them pay a higher deposit, several months rent in advance, etc.

I've purchased my property in my personal name, then transferred them to an LLC.An LLC provides you anonymity (if done right) and it separates your investment from your personal assets so you reduce risk of losing personal assets in a lawsuit.

Such draconian changes to the attractiveness of owning investment property would reduce the availability and increase the prices of rentals without generating significant tax revenue.

The agent advised that I ask an attorney to file a request w/ town to waive off the taxes or reassess to reduce them because they're exorbitant.

With a Heloc-funded downpayment you will be paying off the Heloc + your mortgage debt which would reduce cash flow.

In that case, to reduce the amount of needed capital upfront and to be able to have more capital to get more properties, is it wise to use PMI to lower down payment amount so you have more money left over for another property?