I am going to be hosting a high-level mastermind group in April out of my properties in Costa Rica and I am reaching out to high-level investors to invite them to come.

Still sounds like light work, no more than $10,000-$15,000 ish (On the high end).

When we did it, rates and prices were low enough (and rents were high enough) to still be in a cash flow positive position despite the higher mortgages. 

I graduated from Cupertino High personally. :)

"Should I buy now, interest rates are so high...I don't want to househack in a dirty duplex with a stranger, oh whatever shall I do, wherever shall I go? 

@Catherine Ding  The additional costs of a smoker are the purchase of the ozone generator, and the additional paint prep with wall washing, and a high quality primer coat.

So you're out of luck on that.2nd, it's highly unlikely a rehabber ever has actual knowledge of water intrusion as they don't own a property long enough typically to become aware of the issue.3rd, Indiana is a Caveat Emptor state.

I would imagine just to make something like this pencil, the cap must be pretty high, right? 

You need to be a pretty high wage earner for it to make any sense- I'd say at least something in the $200k range or more.

I would get insurance with an umbrella policy and a high deductible.