One is under contract in which I plan to 1031 into something larger and the other I just plan to keep as the contract expires soon.

I'd like to accumulate enough properties to cash flow 6 figures, which would likely be a 20 year plan. 

Also, make sure that they have money in their accounts in case things don't go as planned.

I'd like to talk to someone who can help him make a plan before this gets out of control.Does anyone have a lead on how I can find his next in command that would be appropriate to talk to at Malmstrom or is there maybe an office for this sort of thing? 

Are you planning to rent it out or live in it?

I’m exploring the idea of buying a vacation home near Yosemite, which I also plan to list on Airbnb.

I'd talk to your broker on what it'll sell for after the fact and where the market is heading over the time you plan to own it. 

Beg family and friends to fund it for you.They "might" do it if they see you've learned a lot and your business plan sounds very solid.How do I know this "might" work?

Just wanted your plan to be realistic.

Present this plan and go from there.