If your home is in a desirable area and priced right, you shouldn’t have much trouble finding a tenant even late in the year.

US was intentionally not built to go in a straight line.

To be blunt, I was cocky and never expected to go so far over my projected budget.  

While house hacking, you're going to learn a lot about property management, rental property finances, and how to be resourceful.i would encourage you to go to real estate meetups and go into local Facebook groups to expand your network. 

If you want to limit debt and use cash it'll be a slower way to go but nothing wrong with that.

Exactly, it's a strategic tool used to entitle land in instances where the base zoning is at conflict with the desired housing density/site plan.

Since I buy in desirable areas, no rent reductions or incentives.

One of the most important person on your team is your financial guy, I'm a real estate guy and I have zero interest in learning all the in's and out's of taxes, in fact I get super angry just hearing about how i'm wasting money to go into a bottomless pit of no where.

If you have term insurance and umbrella coverage, you are good to go.

It is so much easier to plan all the possible scenarios, choose the best path forward, and then implement it in a way that gets the desired results.Rather than trying to recover from an oppps, after the fact.Saving on taxes speeds up the next BRRRR.