The biggest determining factors for STRs in the area are purchase or build price (and associated mortgage) vs rental expectations, that will help you determine net cash flow.

If in the rare chance they do allow short term rentals in the HOA rules/regulations and association documents, don't be surprised if they change that ruling after you buy. 

I recognize that my net worth is small compared to some of the people I associate with.

Cannot control association fees3.

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

I would think that local chapters of builder's associations would be a good spot as well.

Any person over 18 should go through the tenant screening if they are living there...they don't necessarily need to be on the lease, but there is another area on the Chicago Association of Realtor's lease to add occupants.

Leverage magnifies return. 3) The effort involved in adding an ADU is comparable or larger than a rehab associated with a BRRRR.

I’m in northern New Hampshire where we regularly get to -20 degrees during January and February.

And as far as social media goes, there are more than 2.2 billion active users on the site every day.