They are based in Austin, TX, and only want to lend to rent-ready (these are), cash-flowing properties, which makes sense.

Do any of you think a handyman service, focused on helping agents, help their clients quickly makes sense as a business for me?

., so perhaps it would make sense to build at times.I'm opening my LoopNet app right now.

I think you'd generally want to analyze the deal as fully occupied, as you will not be living there forever I presume, and want to make sure the deal makes sense when you move out.

The majority of my portfolio is North of Seattle (mostly Snohomish County and 2 duplexes in Skagit) and you're right, most of the time the numbers just don't make sense.

      I'm curious as to the hypothesis outcome, and think its perhaps 50/50 as to whether this makes sense from a business perspective. 

He is in an upside down position, but the property can rent for $800, so even at $34,000 the deal makes sense.

Now, if your property is valued at less than 50K, then it might make more sense for him to list it somewhere between 7-10 %. 

I think most would agree that using an email address + bank is a reasonable expectation for pretty much any transaction in 2018, much less one with such a high value.I suggest that you should seriously consider either forcing the tenant to adapt to your online management (given that you aren't asking doing anything unreasonable with the rest of your tenants which I presume you aren't) or increase their rent as you see fit to pay for whatever inconveniences you're taking on to accommodate the tenant.You may have inherited the tenant in this "state", but unless some agreement was written into the lease prior, I personally wouldn't see that to be enough reason for you to go through so much trouble.With that being said, I believe 100% in going above and beyond for my tenants and if you feel that this is makes sense for maintaining the brand of your landlord business, I say go for it and good luck!

Not wanting to waste time on phone calls makes a lot of sense @Max Gradowitz.