It sounds cheesy, but the best way to prepare is to work with a friend or two and role-play.

I am preparing for a few years down the road when my kids are in/through college. 

I think its worth a test, but like Jerryl said, you need to post multiple times a week for many months before you would know if its going to work a lot.

You need to always be changing with the market, testing and poking to see what marketing works better and what does not work at all. 

Great, so you are getting prepared to start already!

If you have a regarded tax entity, e.g. partnership, S Corp, C Corp, you need complete financials -- P&L and balance sheet to adequately prepare the tax returns and answer tax related questions. 

R&D is like split testing, trial and error is "I'll be damned to spend the time investing in knowledge so let's just hope we survive the guessing". 

I do suggest putting the asset in the app ASAP to lower the audit risk.You can meet Substantially all participation tests (test no 2).

While most who post about asset protection on BiggerPockets are focused on how to remain anonymous and how to prepare for conflict and liability, the billionaires are out there proactively preventing the liability events from occurring in the first place.

Congrats on preparing your property for an STR in San Diego!