Creating these entities have costs especially the S-Corp so only do what works for your specific situation.

There is obviously a formal lease, and we also supplement with a room mate agreement which outlines the more specific things like overnight guests and expectations in dispute resolutions/ cleaning/ care for the home and appliances, etc.I haven't received one formal "LL request" email yet, other than a formal 30 day notice in the event of a move out, which is usually after they've come talked to me in person about it to begin with. if there's an issue, it tends to be pretty limited to "hey, we have this shower rod falling off"... which im usually here to deal with (and tbh most of the time they like to fix it up with me), and it doesnt need to turn into a big thing. as for keys, i have the house on a yale smart lock, so 'handing over keys' is just official move out, walkthrough of the room for damages, and then I can delete their access code and access to the smart home systems without having to re-key the house. 

It is landlord-friendly, and specific pockets have gone upwards of 2-4x in the last 5-10 years.

Is there a specific strategy that all newbies start with ?

While most municipalities do not possess an interative map as easy to use, once you famiarlize yourself with the base zoning districts that allow the 2-4 unit buildings, relying on the local zoning maps will help direct you to the specific areas within the municipality that possesses the proper zoning.

If you were to use AirDNA paid version as a starting point you could find specific properties and their trailing 12 months of performance. 

I'd appreciate the chance to speak with someone who's done this- ADU development- in this area, either in the City of Walnut Creek specifically and/or someone who's had to experience with being in an unincorporated county area in general. 

I'm using sites like airdna to help analyze deals but would like a little tip on how to navigate local licensing (if needed or not) and how I could maybe start one in Madison specifically what hoops I need to jump through?

if you have BP Pro, there are lease agreements for each state prepped by state-specific attorneys!

Appreciate some feedback.I had a tenant, ironically also in Gaithersburg (hope it’s not the same person because she was a pain in the *** lol) but she wanted a new carpet we paid half, she paid her half via us uppping the rent $50 over what it otherwise would have been, so that’s always a creative option, however I wouldn’t want gas at my property if I could avoid it, always a risk of a leak or worse so I’d probably lean towards saying no to this specific request.