Imagine making millions of dollars over the course of your career and then having to pay 30-50% every year to uncle sam instead of compounding that cash over time.This is exactly what real estate professionals have learned to mitigate.To reduce their taxable income, they just buy a building every year, do a cost seg, and use depreciation to reduce their tax liability dramatically.Their personal wealth snowball grows much larger and much faster than their W2 counterparts who give most of their money back to the government each year.Following this strategy as a real estate professional is one of best ways to end up with a much larger net worth at the end of your career.

i think this is a decision only you can make. im in a similar boat (house hacking my primary) and considering renting the whole thing out to get a solo home for myself. certainly a lot of appeal in that, given how much work goes into the house hack. but whether or not the numbers on cash flow align is up to you. personally i dont think $150 (seems like about 12%?)

Also, personalized post card size info/thank you card with the top 5 restaurant/bars or attractions in the area.

The person I would seek advice from is a CPA about this. 

BUT, let’s say for personal reasons you want to “stretch” for faster wealth accumulation.  

I think this is a calculation a lot of homeowners are making right now--especially if they have a low interest mortgage, equity, and their house will cashflow as a rental.The choice is a personal one of course, but I think your future self will thank you if you pull out some equity from your existing home with a HELOC for the downpayment on the next house and a cushion renting your current home, use a property manager as you have other things to do, and buy the next house and do the same thing again.

A new person moves in and she says the upstairs neighbors are creating a ton of noise.

I was fortunate enough to live in Detroit for several years, so I was able to establish a network before moving back to California.

The absence of a personal guarantee from any disqualified persons is still required, just as with third-party financing.

The question is, what is the intention  of the owner, not what would a reasonable person think is the intention of the owner.