I've also considered doing a "test run" with an SFR in the Cleveland area and if that does not work, simply converting the unit to long-term and adding it to my existing portfolio.  

If you want to list your actual list of remodel tasks, the community might be able to recommend someone(s).However, since you do not have a shovel ready project, many contractors will not be willing to commit time to help. 

Further, the existence of a diving board or slide further reduces that number.  

Your talking about purchasing all new baseboard units, having them installed, all new electrical wiring run and either a central thermostat or room based thermostats.Regarding your existing furnace, did you only get a parts replacement quote from the one contractor?

The existing triplex is detached and built along the outer edge of the property line -- probably long before the current zoning rules went into effect.

and I spoke with the bank earlier today and confirmed that we should qualify for a jumbo loan that would allow us to make this work out.The place I am getting stuck is trying to figure out any kind of realistic estimates for whether the three cabins are actually able to generate enough positive cashflow to allow us to eventually step back from our jobs and/or running the numbers for everything in a way that I would feel confident enough to try commit to something like this.Would it make better sense to try and start out with something more simple/conservative?

Call me about some ideas to contact existing trustee and servicer

I use 5% too and ask for a copy of bylaws, who the management is, make sure the board exists and is current, check reserves and future expenditures.

An investor only needs to understand the market dynamics in this area and exploit the existing potential.

The existing pattern will continue3.