Just today I found out that I'll have some "boots on the ground" in Tucson so I expect I'll be out that way in the not-too-distant future.    

We could buy in either HI or TX market however we're considering the Hawaii market for this purchase as we plan to live there (now/possibly retire there in the distant future) and could capture more real estate with this loan vs the Austin market.Goal: with this in the end is almost entirely for a long term hold appreciation play so although cashflow would be nice it's not a requirement as we have about a million in liquid assets to weather unforeseen financial storms (or buy other properties). 

The key is finding people you can trust in those distant markets because you will be relying on them to get you information and you need to make sure they are knowledgeable and reliable. 

My advice:  It's hard to "cut your losses" and tear off the band aide, it will feel a lot better quickly and soon be a distant memory. 

I’m using feedback here to determine how helpful, what and how much these would be to provide this service in the not to distant future.

I'm trying to work out a model for distant properties and how or what to work, etc.  

We have so far let all friends and family (including distant family) stay for only the cleaning fee (and I would pay the cleaning fee for my guests who were low income).  

I think my concern is going to be that roof and any other major repairs that will need to come in the not-too-distant future.

He only had one distant Cousin left in the family.

Is there a chance either of you will leave your w2 and qualify for RE professional in the not too distant future?