UPDATE - I quit my job and have a 2nd roommate.
Like Laura33 pointed out, it comes down to a lifestyle decision. I've been unhappy at work for a year, which is just not like me. I don't feel like I'm doing a good job, either. So I quit. It was hard and scary. I really hope I don't regret it later. It was also incredibly freeing and exhilarating. So much feels possible now. I love being engaged and busy at work. I was bored. I would rather have 2 roommates indefinitely than continue to work at a job that makes me so deeply unhappy. Even at 3 days a week it bleeds into the rest of my life. I like having people in the house for the occasional social interaction.
I'm still working through what's next. I don't *need* a job but I may want one for emotional, social and extra-cash reasons. I'm making (slow) progress on a prototype, attending tech conferences and focusing on being more active. I have a verbal job offer from another company but I don't think I'm going to take it. I want some time to re-set.
My 2nd roommate is moving in tomorrow. I turned down about 20 people - the rental market here is hot. If this roommate works out the way I expect, I will have $2040/month or $24,480/year coming in. I am keeping the last room as an office, though I may rent it in the future once I see how much I use it and how it feels with these 2 roommates.
I think you should calculate the true cost of your home, including property taxes, maintenance, major home improvements. And then check if your renters really cover the cost. Because you are picky, your rooms are standing empty for quite some time and that is costing you money. I think you should consider downsizing to a smaller home that fits your needs. You will get less maintenance, lower property taxes and less hassle with room mates.
I've though about this a lot but it doesn't really make sense for me to downsize unless I leave this city and live somewhere cheaper. Property taxes are grandfathered in, so I pay about $3200/year in property taxes. Buying a similar home now would run me around 7K in yearly property tax. Even if I downsized I would still probably owe more in property tax. I have 4 bedrooms but the house isn't actually very big, compared to the ones around me. I guess I could give up the yard and move into a condo but I really like having a yard with stuff growing and birds.
Maybe someday if I decide I don't want renters, I will need to revisit this. Another option is to rent the entire house (for about 3K/month) and live somewhere else for a while.
Finances_With_Purpose - thanks for the resources. I will look forward to checking those out.
Manchester - I have considered AirBnB. Might be a fun option in the future.
MrThatsDifferent - I do have about 75K cash right now. My tentative plan is to live on the low end of my budget for now so it would be maybe 4 years before I need to touch investments. If I live on 40K/year thats 24K rents + 16K cash (with some extra cash to cover lost rents when I need to replace roommates).
Sunflower - thanks for the encouragement!!