If there is a much easier or cheaper way to collect the dues I am for it.thanks.

Duplex can always add additional units via the ADU laws. 8) Related to number 1, purchasing a property with an existing ADU is cheaper than buying a property and adding an ADU.

Does size of mortgage paydown become a factor here?

At least in my area, it's cheaper to own a condo with the HOA dues than it is to pay for all the utilities, snow removal, waste management, maintenance, etc, that goes along with an SFR.

Hiring a lawyer sounds expensive, but it is way cheaper than hiring a amateur (in this case yourself) who costs you money and provides no results (and then you need to hire a professional anyway).My personal philosophy is to "do it right, or do it twice" and its way cheaper to do it right once. 

Those are probably cheaper than hard money anyway. 

You’re in a great position with a property that’s appreciated significantly, a low-interest mortgage, and clear goals to boost cash flow and transition into full-time investing.

I have to choose between a much cheaper market that I live in that is much easier to cash flow, but finding good renters could be more difficult.

There are cheaper one’s in D/F areas but I would be careful as those can create a laundry list of additional issues.

In your example, $250 in utility bills is much cheaper than $2500 to fix frozen-pipe damages!