@Chris Aronson Those numbers don't seem unreasonable, although from a cash flow analysis perspective you can remove your own utility bills from that number (those are resident figures and you should care about them for your personal budget, but they are not important when evaluating the property - a future tenant will pay them!).

Option 1: the 50/50 splitWe can just decide to ignore the differential in hours required by each of us to keep up our properties and can split all returns down the middleOption 2: billing the partnership for his laborWe can determine a reasonable market rate for his labor beyond a certain number of hours per month, and can bill the partnership for his time.

As far as the property tax implication goes, you're talking about two attached structures, therefore should be one parcel- not having two sperate tax bills it seems. 

A new bill introduced by DC At-Large Councilmember Robert White would allow D.C. to pay landlords to turn existing units into dedicatedaffordable housing: https://ggwash.org/view/81507/....

This bill could come up for floor vote as soon as this week.

Essentially we want a vacation home, but we'd only use it a couple times a year, so why not have renters pay the bills!

I am looking more so in Montana (Billings and west of that) and Idaho.

The owner had several properties for sale, but this one fit the bill pretty perfectly for what I was looking for.

Thank you @Bill Exeter

Or get a job with a mortgage broker so you can learn how the money moves and be exposed to numerous sources and options for funding.