One friend of mine had a client who recently tried running an Airbnb in a little Craftsman duplex near North Park.

I’m hoping to not build until I acquire more revenue from profits of the plot via flea market, parking, boat parking, or something else that requires minimal investment.

The DSCR program "Must use the lesser of the two either common rent from the appraiser 1007 rent schedule form on the appraisal or the lease".You also have to factor in the taxes and insurance because a guesstimate or ball park can kill the approval. 

In my devious mind, I thinking like you that I hire a parking attendant, install gates and charge an entrance fee if I bought it. 

Oregon has officially declared war on rental-property owners.

You may pay 1.5m and up for a good one, likely more if parking and balconies, but the play is to buy a multi and then wait and in a few years, turn them into condos and sell them separately - that's how you make the money there.

Our rent-by-the room residents appreciate a lockable bedroom door, a private bathroom, sufficient on-site parking, a large refrigerator and a large washer and dryer (in order of most to least important).

Those buying close to the city are either breaking even or taking negative cashflow and banking on appreciation (or buying all cash and parking money, ha).If you do consider Lowell, I'd also recommend you check out the Fitchburg/Leominster area as well.

Two Reasons: First, because 50M people in this country either work gig jobs or are illegal immigrants, when they lose their jobs or have their hours scaled back, it doesn't show up on official unemployment stats.

Chicago has so many awesome neighborhoods and Humbolt Park is definitely one of them!