Starting smaller might help you gain confidence and reduce potential stress.In your situation, if you're comfortable hiring a property manager to handle day-to-day operations while you’re working in the oilfields, going for the 4-plex could make more sense, especially with your high income.

As someone who started buying with buy and holds back in 2005 and didn’t start wholesaling until 2013 I believe wholesalers who operate in integrity and with character bring a lot of value to sellers and buyers in the market.however Having the resources to be able to close  on deals and then if we want wholesale them has been invaluable to our business. 

@Alecia LovelessWho's operating the heavy equipment ?  

@Chris Seveney I am not sure if you're hearing this more often than ever, but I hear similar stories weekly in about four markets I operate in.

The STR deal could be the best option if I understand your situation correctly, except I would probably do this as a cash-out refi and just use the combination of booking history + AirDNA projected income to qualify (if not operated as a STR for a year).

We operate nationally and I work with my clients in DWF out to Tyler and a bit in Houston.

I am no expert (hence posting here) but the bit that I have read seems to indicate that if the business is located in CA and operating in CA (as is the case since the property is in CA), the business is likely to fall under CA laws in the event of an issue. 

At the end of the day though, you still couldn't operate a car well by just reading about it.

Regulation has slowed the market and made it harder to be an operator.I've never operated my Airbnb to its maximum efficiency because of the time it takes. 

The folks staying in your unit want a seamless transition to their new living quarters, and the person paying wants an easy way to cross out that line on their to-do list.