The main reason is because local governments are getting quite aggressive trying to shut down STRs and creating new taxes etc for them.

It can be done right but more often than not, it's done wrong and can cost investors a lot of money.

Finally (after 7 years of reading books, research, podcasts etc) jumped off the cliff and bought a major fixer upper for very little money.

I live in Ann Arbor and it's a really tough investment market because of the high values and taxes.

The idea that you can build wealth without putting any money into it is a recipe for disaster and the sales pitch of gurus trying to steal your money.

With the current market, I will not be able to make my required cash flow after paying all operating cost including mortgage, vacancy, property tax, insurances, maintenance cost, no need for a property manager because I can manage it.

Before that it was primary residence since January 2019.Do I need to sell it this October to avoid capital gains tax to qualify for 2 of last 5 years exemption for capital gains (up to 250K single, 500K married filing jointly)?

In addition, some reserves should be available to handle any large unexpected issues that crop up before money accumulates to pay for it.

Not a lawyer or tax person or anything. 

Considering them for a hard money loan on a flip.