You should also familiarize yourself with landlord-tenant laws and regulations specific to the market you choose.

Research the local regulations.

I've reached out to the City of Winston-Salem to gain more information on tiny house regulations since there was not much to be found online.Thanks!

Lenders face far more regulations when lending on owner occupied properties which may limit your options.

Hi Jacob,I agree with Bruce, if you can show up or call the HOA to find out their stance on 30 day rentals this would help you figure things out better.Ask to see the HOA's Bylaws and CC&RRs (Combined Community Rules & Regulations) to see if there is language that allows rentals/leasing (without restriction).If there is, determine what the criteria is for amendment changes to the CC&RRs.

Definitely look into STR regulations in any area you're researching.

Also, based on the new regulations (1 of the 2 units must be owner-occupied), how do you think this will impact the home's value?

Too often we see Landlords keep rent down to reduce headaches, only to find out later that they can't raise rent due to rent control regulations. 

My question is, can I use one of the separate parcels as collateral for a construction loan to build a multifamily on it (of course adhering to zoning regulations)?

Understand Local Laws:Familiarize yourself with local landlord-tenant laws to ensure you comply with all regulations.