I've heard of people doing it 'under the table' but what's the best way to do it for both parties? 

We would be installing a street and double stacking townhome style units on each side.I part I don’t have experience with necessarily is how to better understand infrastructure and site work cost (road, utilities, excavating, etc.

Also which party in the home buying process would be looking for these things ?

Thanks Adam .This is great .Will do what both you and John suggested .I am hoping the bank uses a third party appraiser.I assume there would be laws against them using an “in house “ appraiser..I just know they’re not going to want to gibe up getting that $250 a month from us ( PMI).Much appreciated -Christian 

Get an appraisal from a disinterested party.

For instance, I was looking at a property for STR in a town in VT and the realtor explained the town passed an ordinance preventing repetitive short term rentals of properties because of partying and noise violations. 

How this capital is accounted for depends on any agreements made between parties. 

Polite and their very rare parties were not wild - no noise complaints or anything.

We’ve had 6 showings in the past week alone, which is already a lot, but the most concerning part is what’s been happening during these showings.Here’s the real kicker: there have been showings (with prior notice given) when we weren’t home, and my cameras caught prospective buyers entering unaccompanied—no realtor, no landlord, just strangers walking into my occupied home.In one instance, my husband happened to be home and answered the door.

Good LuckTypically multifamily is 5 units or more and Single Families are 1-4 units, so I was confused, so thanks for the clarification  Actually, that part is only half true because there are additional criteria that need to be considered to be multifamily vs SFR, such as separate utilities, heating systems, how they are attached to one another (Vertically vs horizontally), etcan easy way to differentiate and communicate is to call it multifamily if it has more than 5 units. and Single family for 1-4 units or call it how it is duplexI own several duplexes that are considered single-family homes by the city.In the end, it is your decision on how to use it