On a C2 parcel with existing occupied income, the lender will care a lot about the as is DSCR on the current triplex plus shop, your plan and budget for the ADU or duplex, and whether the entitlement risk is real since the CUP and planning approval can drag.The actionable step today is to get a lender package together with current rents and expenses, a pro forma rent for the new units, a rough build budget, and your best guess timeline for permits and construction because that determines if you need an entitlement loan first or a true construction draw.

By using a portion of your stock market gains as a down payment, you control 100% of a physical asset’s appreciation and tax benefits while only committing a fraction of the total value in cash.3.

Beyond basic numbers, how do you stress-test deals to make sure funding won’t become a problem?

We worked out a lease option deal whereas the renter will rent the home with option to purchase in the future, put down $25K for the option and pay 3x the current rental amount with some of that money paying down the house all with a 3-year balloon and 3-year lease agreement.In this scenario Renter can purchase the home at the end of the lease at a predetermined price favorable to owner, renter lowers their existing monthly output by over $8K per month, owner gets a quick $25K and substantially more rental income over next few years and if renter defaults owner keeps $25K and additional rental income. 

Now, normally, I would emphasize the importance of touring a property before making any commitments, but this particular situation seemed promising ... at first.You see, we had the vacant units and the down units all ready for our visit.

I know these types of people exist, but I don't know where to find them.

So, again, it's generally not a good idea to use a credit line for long-term commitments.

Before committing, demo a couple and make sure their reporting and bookkeeping play well with your CPA or accounting system.

.: Quote from @John Underwood: Quote from @James Carlson: A bit old-school here, but unless you've got multiple properties, I'd use Airbnb and save the money you'd spend on other platforms.Maybe I'd consider something like Turno to connect cleaners with your calendar, but most of my STR investors in Colorado -- even those with 2 or 3 properties -- are using Airbnb's existing automated message capabilities.Others may feel differently. 

Sometimes you can get away with a builder's risk endorsement on an existing landlord or homeowners policy.