We all know what goes on in bathrooms and what kind of extra care they need.

15 - 20 year hold time.The rental investment calculators show that the four $300k properties would have a lot more equity in the future and many times the cash flow after a few years, but does the extra maintenance, management time and expense, etc. outweigh the numbers?

Make the rules such that the tenant, in order to get the extra federal unemployment, must pay at least half of it to rent.

Is it worth to invest and learn from their program in order to start my co-hosing STR side business just to get some extra money monthly?

It shows you are serious and willing to go the extra miles to make it work.

Like maybe I could pull enough out from heloc on primary residence to pay off debt and then rent out my primary and use the extra cash to payoff heloc and then do another heloc once the original one is paid off.

At some point that market becomes saturated, pushing revenues down and the extra juice won't be worth the squeeze. 

It 12 years, assuming you make no extra payments, you'll have a paid off condo that cash flows a lot better. 

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

Otherwise perhaps your winter people will pay $500 extra if your cap is $500 and that is not what your competitors will be doing.