Sometimes there's cool products that are regional or offered at local credit unions.

I have nailed down a list of 10 different cities/regions I would like to live in.

Particularly in the Denver CO region?

Unfortunately, cash flow negative investments are not sustainable, so your decision really becomes one of, how much negative cash flow can you support.You have to assume a lot of variables for these types of calculations but in general:[(Purchase price of duplex x % appreciation x years owned) - (closing costs from purchase and sale) - expected cumulative negative cash flow + expected tax benefits + equity from principal paydown] - [theoretical investment with cash on hand now plus monthly reinvestments of negative cash flow above for the same time period you us for years owned - expected taxes from theoretical investment]That exercise will give you the return or cost of your decision to house hack.

My "test" was a tenant that I could not get rid of, in a tenant friendly region.

If you already have two+ mortgages, I'd honestly call local credit unions and regional banks.

Lawn care is typically the responsibility of the tenant.These are all general answers and every region is different so look into other listings and see what they are doing. 

Is there anyone in this region that would like to grab lunch and share experiences?

M&M Lending is a regional private lender who funded this project.

this is highly regional.. there are still large parts of the US were existing stock can be purchased and remodeled for far less than cost to build new.. especially with material costs right now..