They seem  high to me, but I'm not actively renting anything in Denver right now and I am continually surprised by the prices I hear.I think you're being smart, and I think the boyfriend is being sulky.I'd probably buy the triplex and dump the chump...This didn't answer all of your questions, but then you do have an awful lot of questions packed into that post!

@Gil Estupinan  In-N-Out never goes out of style!  

The kind of property your looking for       (Min. bedrooms , style you would like, commercial or residential, one owned by a clown, etc)2.

Compare this to places like SF or NYC where few places to expand to and old style rental regulations constrains housing supply to a certain number of units a year so you either buy the higher prices or move. 

Townhouse style near downtown might do better, but price point is much higher.

@Mike Pauze if you are looking for a renovation style loan, search here for Alex Bekeza...he works with investors and is active on BPIt's important to define the loan product up front...some conventional lenders may not have the product you are after.

Get it styled woodsy to fit your cabin resort dream and make this the first step to making your dream a reality.2.)

Houses that look very similar on paper (same neighborhood, style, square footage, year built, beds and baths) can have very different market values depending on things like interior light, flow, ceiling height, privacy, yard space, neighbors, curb appeal, master bedroom size, kitchen counter and cupboard space, parking options, driveway slope, proximity to noise or businesses, parks, schools, etc. - to name just a few things. 

Anyone versed with this unorthodox style of purchase? 

I'm nearing completion of my flip in Kingsessing, and while I've seen listings with virtual staging done, I am considering going with an actual home stager to give prospects tangible styling possibilities.