You are in a great place to learn based on the successes and failures that many have had.  

Just keep in mind that there are further steps you'll want to keep to minimize the possibility that your entity is ignored for this kind of personal liability (say, if you were the person who didn't properly clear snow, or if your finances and the LLC's are comingled).And I agree with @Chris Seveney, insurance may provide adequate protection based on what's available to you.

My opinion varies based on my experience, and keeping a property manager has been a nightmare for me.

It really becomes a time value of money calculation based on when you want to sell your Class A rental.

Would you recommend the route of a first lien HELOC based on the above situation and information?

@David Cook this is why we’ve started using water based polyurethane on our hard wood floors.

In almost all investments, you should have a solid base of reliable, cash-flowing, and hopefully appreciating assets before striking out into something new or riskier. 

Should he be exposed to all liabilities that comes with it such as lawsuit, history of insurance claims(I believe insurance have a data base of past claims that can affect future coverage), credit and what not at an early age? 

SO expect to pay a premium based on what the potential value of the building can be once maximized and stabilized.

I've got the idea to more positively incentivize my tenants to pay rent by the idea expressed in the following example:- If they pay any later than five days late, they pay base rent ($1,000) + fixed late fee (e.g., $150)- If pay on time without autopay, they pay base rent ($1,000) + "manual payment fee" (e.g., $25 or $50)- If they use autopay for timely payments, they pay just the base rent ($1,000)In the above example, you see that a discount of $25-50 was applied in the case that the tenant chooses to setup autopay to schedule on-time payments via a given PM software.Please let me know if any software comes to mind and also any feedback on the positive incentive idea.Thanks in advance!