My buddy John and I had the above discussion years ago before he died. 

I stayed with a buddy in Roppongi Minato  when I was there.  

I was chatting with some of my lending buddies at big banks and they are all backing away from the CRE space including office because operating costs are increasing more quickly than rents.

I have a buddy who offered sponsorship, but he has been doing it for over a decade and maybe only sells one house a year, and never to investors.

My buddy's 3-flat just sold for $100K more than what he paid for it a year earlier.

A buddy of mine who invests out in Phoenix once had a client facing a similar timing mismatch on a rehab project.. they ended up working closely with a local credit union who was more open to interim valuations.

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

My buddy almost always does MTR and if there isn't any bookings then he will do an STR. 

My buddy learned a lot from this club and was able to acquire (3) SFRs doing it part-time while working full-time at a car dealership.

If that market fits what you are looking for and it's closer then I would invest there, but if it doesn't fit what your looking for from a metric standpoint I wouldn't just invest there because a buddy does. 3.Being able to get a direct flight helps, but I wouldn't make a decision on a market based on that4.