Heck, have him send you $50k for his half of that dream $100k vacation you plan to take next year.

This will allow you to acquire more rental units and also being able to use the vacated unit rents at 75% to help your debt to income ratio DTI.There is a FHA 100 mile rule if you do plan on using FHA on your 2nd house hack.

Have you considered vacation properties in California?

Tourism and Vacation Rentals: With famous attractions like Disney World, Universal Studios, and miles of beautiful beaches, Florida attracts millions of tourists annually.

I didn’t know anyone that owned 1 rental or even 1 vacation home.

Quote from @Taylor Williams: Navigate to Real Estate Strategies > Short Term and Vacation Rentals, then search for "arbitrage" and read what others have to say.

I know personally when im looking for a place to stay if its a little more pricey my brain usualy jumps to "oh this place must be better than the others" since this is a heavy market for vacation rentals and not traveling professionals I could see that being a factor but it makes it very difficult to price and what price point to risk.

I live, work, and operate in a traditional vacation market and a booming up and coming city, Tampa FL. 

I have a townhome in LA that a family member is vacating soon.

People just don't want to be cramped up when on vacation or working remotely.