It depends.

The members here on BP that talk about STR auto-run systems didn't install those systems and find dependable cleaners & handymen overnight.

Depending on the seller, you may sweeten the deal, by letting them know that they don't immediately need to cash out, or can partly cash out.

I find that depending on the market $300-500/mo are fairly normal and if compared to what you would pay with a single family home on some utilities, maintenance, and management, it's a good deal.

There are definitely options for less than $100k, just depends on how much lower - $75k is doable but less than that gets a liiiiiittle tricky (although still doable in some cases).

Alternatively, I have spent the last decade doing technical work in cybersecurity, and can land a job between $140k-$190k (depending on where in the US). 

I think it depends on the individual and opportunity.

Your success depends on it.

Depending on how far values decline is the difference between a partial loss and total loss. in essence its the same position of those who make second loans behind the first or third position when pref goes in front of you..

For example, an ADU is nice for a rental, but not every home buyer wants to pay a premium for an ADU on their property.This would be case by case and property dependent.