If fixing up a property just isn't feasible for a seller, it must be reflected in the price in order to compete.

This would allow us to no longer spend any money on rent and our AirBnB tenants would fully cover the costs of home ownership.So my question is, how feasible is my plan? 

We could feasibly rent out the finished basement for around $1000 per month, if not a bit more.

Lastly, is it feasible to do 100 or more of these claims a year? 

It wasnt feasible at the time but I started educating myself about the process.At one point a few years back my company decided to upgrade our office digs.

So are you basically saying that if legalization is not feasible, you don't want to keep it as is, or connect inlaw space to main house?  

really depends on where your at in Oregon City.go into public works and make sure your sewer is gravity and sized big enough.. and your water etc.some lots IN OC are just not feasible to split.  

Granted, ever since the spring of 2015 I have been exploring various ways of making money (photography business, stock trading...) and had taken numerous action steps but nothing seemed feasible as I waded into the unknown, nor were they aligning with my strengths and passions.But.Real Estate.The Potential.I immediately searched out and attended several REI clubs in the Houston area, witnessed a couple case studies by 'average people working day jobs' and my mind was blown.

Hi Joshua,Speaking from experience in WA state, which may differ from RI, you should write an offer with a "Feasibility Contingency" of 30-60 days and then ask some questions at the city zoning/planning department.  

That would definitely be feasible if this were more typical Milwaukee duplex, as they usually have a walk-up attic.