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.

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

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.

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?

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)?

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. 

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

Quote from @Heather Rummel: You can manage it on your own, but it takes a lot of work to educate yourself, particularly in the most heavily regulated corner of the world.I would start by calling around to property managers in the area for help.

Start by checking into regulations.