For real estate/investing, I have found that an understanding of finance and accounting can be the biggest benefit (if he can take extracurricular courses on sales too that would be helpful). 

While this might seem like a downside, it's important to keep the bigger picture in mind.If you’re looking at a duplex in a good area, close to your work, and the numbers still make sense—even with those lower rents—don’t let that deter you.

Their biggest problems are things like:“my net worth is $10M and $8.5M of it is in my three properties I purchased 25 years ago.

There is a bit of upside and downside for you but worth the risk/reward for what feels like a cleaner break

.: What are the 5 biggest mistakes seasoned investors are making here in the forums? 

It's the biggest feeder city there is besides NYC and also one of the most glamorized tourist spots in recent years. 

However, in this case it’s worth circling back in 3 months, 6 months, or a year because this seller wants to sell, he’s just not ready to give up his fantasy deal.If the seller’s response is acceptance of the outline of my offer but countering on price or terms, it may be worth negotiating because we MAY be able to get to YES.My biggest profits have occurred when I made offers that were nowhere near what the seller was asking and yet WERE ACCEPTED, or with small modifications. 

I also BELIEVE their biggest concern is tax liability shifting.

I agree that the swarms of "my market is great, contact me for more info" tends to be the biggest problem but a lot of that will depend on you, the poster - as @Russell Brazil mentioned just hit the report button on posts and we can check them out faster. 

The biggest issue that came with this method is that it still works great for VRBO, but now after an AirBnb booking I have to ask the guest for their email to get this process started.Zapier is also monitoring for the returned signed RA and that point then sends out all the info the guests needs for their stay.The rest of the email automation is handled by the PMS.My biggest pain, is when I get a difficult guest, or when things break mid stay.