My name is Paul Ewing and I became a semi-accidental landlord in early 2012 when I bought the farm across the road from my that had a house and an older (1970s) singlewide. 

For the vacant units, I'm leaning towards weekly or semi-weekly checkins with the topics for discussion being how many showings, applications, etc. and also whether any specific feedback on the unit itself (in case that it actually the problem). 

Even though you would have to do it semi-annually or annually for it to make any real financial sense, I think a free iPad or the like would encourage people to give reviews. 

Looks like they had semi gloss on walls and ceiling.2-bedrooms I've always had flat on ceiling and walls eggshell?

The house is on 10 wooded acres in a semi-rural area.

Thanks for providing an amazing platform for a semi-investor like me to learn the ropes of REI with the impressive quality of people and breadth of strategy/tactics that are so easily accessible.As for a little background, I'm in sales/business development for a software startup and have been living in Seattle for over 10 years.  

As long as you are willing to be at least a semi-active investor after you retire. 

It should cash flow around $500/month... using semi conservative assumptions.

When I semi-retiree from my corporate job in two years I may look into retaking the classes and getting my license then since I might have time to play the retail side of things. 

You'll have no shortage of people who are interested in it at that price range(50/night = 1500/mo for a bed, 70/night = 2100/mo), and that puts you at around 5-6k/mo with 100% occupancy, and since your rates are semi-competitive with long term rentals but you're offering more value(furnished, short term), you shouldn't have much trouble reaching those numbers.