Today, that building generates enough passive income to cover his annual retirement contributions.You mentioned taking the 10% penalty, which I’d only recommend as a last resort.

Home prices will likely vary by region, with modest increases in areas of high demand and stable job markets, while others may stabilize or decline.

As far as I know the prices have continued to be stable or go up.

I have a good FT job in education administration, but I want to retire asap, focusing on RE (so, not really retiring, but you get the idea).

When valuing the property, focus on its net operating income (NOI) and use a cap rate that reflects Section 8’s stable, government-backed rents.

A general rule of thumb though (not a hard rule) is that if a market has a prolonged history of vacation rentals such as towns whose commerce is very dependent on tourism like beach or mountain towns, then there is a good chance than those towns have established their airBNB regulations decades ago and are likely stable.

Certainly not by liquidating their retirement accounts that just suffered an historic drop in value.Do you feel that Oregon’s bias against landlords is a temporary fad, or a permanent change that may even worsen over time? 

It is great to hear you have goals to retire in 15 years.

.$500k annual income is alot for your average folk, but it's not "retire me" income at all.

My strategy is buy & hold for stable cash flow with some appreciation over time.