If your expectation is that your wife/kids will start selling properties to pay the bills, you might want to have a small amount to help cover any initial liquidity problems they might have or count on them selling below market rates.2) Do you have business partners that will need to be bought out?

If you are counting on it then you should meet with the building department to review status and see if it can be approved.

For each of the areas you might be interested in look up "unemployment rate, appreciation and inventory. year over year"Appreciation (%)(H) Median List Price Y/YInventory (%)(K) Active Listing Count Y/YUnemployment (%)I plot these numbers each month in a spreadsheet and look at the trend.How did I pick some areas first you might ask??

Current room count is 7 on Airbnb, income is about $5000, overhead is 2k of that and I live on less than a $1000 per month so there is a 2K surplus after overhead. 

Lol I see your post count, playboy.

@Tyler Volk it will need a source of heat (as well as being insulated), a legal means of egress, and probably a closet (to be counted as an additional bedroom for resale).

It is mostly based on BR count and size/type of yard. 

I will then have 60 days to return those withdrawn funds ($20k) back into my Roth IRA (I'm sure there is a way to do so instead of counting it as a contribution for the year somewhere in the portal).

You would benefit on knowing some buyers you can count on.You might do what is called "reverse wholesaling" where the buyer finds out at first to know what buyers want or what they are looking for. 

If you're okay with what is basically a tiny home (they can be very nice), then you might be able to get close to $100k but it will be close.From a lot coverage standpoint, if you're under 800sqft or 1000sqft in CA, typically you are exempt from lot coverage issues.On the comps and appraisal issue, the adu comps should count towards square footage, but that doesn't necessarily mean it will appraise at the same cost per sqft as the rest of the house.