Newer homes seems to command something close to $1 sqft up to 1500 sqft then the larger home prices do not scale accordingly.

And people who check all 3 boxes that I mentioned are very rare, so they command and are worth a premium. 

HOA president keeps saying that he can't just fix my roof on his command, it has be approved through the new PM company.

I don't know of any place where a $100k home will command a rent of $2,000 per month.

Trust god be a good person follow his commandments and the rest will fall into place.

@Samuel Chua properties in different neighborhoods can command different rents even though varying prices.With your small variance example it may just be amenities, finishes, Bed Bath is it a 2/1 vs a 3/2 and what is more desirable.

Does it take command of ones cognitive functions of reason and decision making?

The prices of property that are right inside North Conway can become expensive, but if you look at surrounding towns (such as Intervale) you will find cheaper properties than can command substantial rents.

As mentioned above, Portsmouth is outrageous, but commands a very high rental market.

If you are looking to be easy on the eventual owner - and perhaps command a small premium in sales price - you can build a 1200 ft^2 energy efficient (lookup: Passivhaus) home, where the end-user's energy costs could be as littles as $250 - $500 per year.Capital costs to build a Passivhaus will be a little higher (10 - 20% pending on available skills and experience in your area) here in NA, but the end result is a home that is 70 - 80% more efficient than what is typically being built.