Transited Oriented Housing is  a very good strategy. 

Find something that you can enjoy and still make money.As @Frank Wong mentioned your expenses will continue to rise and while $4,500 a month seems like a lot there are always unexpected things that happen in life that will be more than $4,500.A few years ago I was burnt out as well with my corporate job and went through a career transition. 

I burned the candle at both ends before transitioning full time to REI. 

They also changed height limit of detached ADU with half mile radius of major transit stop to "18 ft  plus an additional 2 ft is allowed to accommodate a roof pitch that is aligned with the roof pitch of the primary dwelling unit".I'm sure other cities will follow suit very soon. 

So from a rideshare perspective, I would not do it.Unless you are near a public transit station or stadium, I would say it does not make sense. 

I am still trying to transition some of the legacy tenants to Cozy, and I may run into issues as they are older and also don't speak/read English.

The terms for the bridge loan will be similar to what you mentioned in your initial post, but having both the bridge & long term  products with one lender allows for an easy transition once the property is stabilized.Feel free to PM me and I can give some info on a lender I work with

I'm interested in moving into the property management and was looking to connect with someone who has their own PM company to learn more about how they transitioned and what has been their experience. 

We transitioned out of our W2 jobs "abruptly" about 10 years prior to our anticipated time frame.

I plan on transitioning more tenants to this service.