The biggest hurdle is accurately estimating how long it will take for you to complete your project as HML/bridge financing can be very expensive.

I think it'll be a high hurdle to sell and reinvest- you'll pay fees coming and going, and will probably have some taxable consequences as well.

I didn't have enough disability rate on my first VA loan, but I am 70% now and I'm sure that clears the hurdle (60%?)

I don't want to be unreasonable, but based on the blogs I've seen it's best to be overly clear about what is and isn't allowed!

Keep doing that till you got a portfolio.FHA loans have a few hurdles but are well worth it as they are 3.5% down.

Folks who tend toward absolute returns  have looked at their 'why' for investing and compared that to their available capital and investing options to set a hurdle rate that every investment must meet.

If you’re almost broke I’m not sure how you’d jump either of those hurdles.

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!

He's super busy, so I wouldn't want to waste his time at all.However, I see number 3 as a huge hurdle for multifamily. 

Be prepared for them to do stupid things based in unreason, and take actions that would forestall these stupid things.The discussion I mentioned is part of that strategy.