Your best bet is to speak with a real estate attorney re: right of first refusal. 

That’s the best bet.  

I think your best bet would be to get experienced at estimating the rehab cost.

Typically you'd only calculate long term rent when you crunch the numbers, but Santa Barbara has a shortage of hotels/places to stay, so airbnb/short term rentals, like @Rohme Williams said, should be a solid bet.

Cheaper on the install VS other flooring choices like luxury vinyl plank and tile but far more expensive in the long run. 

Picking a specific market and understanding trends from there by using local resources will be your best bet for success.

That would be my next choice. 

@Brian ChoiI would say your best bet may be to ask if they do commercial loans if you are looking at an apartment that is more than 5 units and if they do lend on that show them the numbers using the calculator so you can present yourself well rather than just being another voice on a phone.

@Matt Small If you are indeed separating amicably you can hire one lawyer/cpa to arbitrate or help you see the pros and cons of your choices.

I think your best bet is putting 20% down with the 20K.