They want a safe, clean, functional home for a fair price, to be treated honestly, responsive maintenance, good communication, and to be left alone.

Then move to an Apartment.[ my concern with this option is that because the house is so big and the layout not really functional for a rental or airbnb, I dont really know if renting this place will work unless I did a major rehab.

I'm an Interior Design Professional and after traveling the world I came to understand why functional design is most important.You guys really did a wonderful job.

Cap rate becomes functionally irrelevant. 

If a tenant drinks heavily but is very functional, not much you can or should do. 

That's where cash flow comes in handy.Problem is, cashflow can always be bought (it's just a function of how much you ultimately put in), so it isn't, in and of itself, a terribly meaningful metric.

@Jared P.Quickbooks is an accounting/bookkeeping software that is used to track your data(income/expenses/assets/etc).If the property types are organized in a separate entity type, I would have them in two separate files.If they are not in a different entity type, you may want to use the "class" function within quickbooks to distinguish the asset classes.With that said, you may want to still operate them in two separate files if you find it that both businesses are too unique to another.

Or a Tentative Map Waiver, with a lot consolidation parcel map...this would allow you to create 2 'condos'...that would both function like separate parcels instead of a normal condo.But as far as legally, simply separating the lot your parcel segregation is the route, and only works if you demo the buildings.

In particular stuff that will not have much of an impact on the appraisal as long as still functioning like roof, siding and windows.

Many brokerage firms will open "free" accounts (i.e. no setup fee, no maintenance fee), which will also come with checkbook access and the ability to wire funds out such that they function as a "hybrid" between a bank and/or brokerage account.