It seems like the trend is to make offers waiving the inspection contingency or having a short inspection contingency period, which makes it almost impossible to get a good idea on what repairs are needed and how much it will cost before I'm committed to the deal.

If you are selling it you would want to make all of these repairs (and more) anyway to get top dollar. 

She’s apparently been staying in it all week & decided the night before the repair to get a $168 room at the Marriott.

So if you have a $200K house, you don't have to have $200K of coverage -- $100K would be more than enough to pay for any repairs -- plus whatever amount of insurance to replace contents/belongings. 

Biggest thing that rookies forget is expenses & repairs, stuff comes up, dont spend the money!

Planes/Trains/Automobiles, Oh My!

If you can take a repair, take the repair since you won’t have to recapture later on.

"$20-25k for spiral stair case install and remodeling of attic = $542,500"Details please: What were your costs to repair/rehab each apartment, common areas, and top floor/attic apartment? 

Both of us on loan, we get owner occupied interest rates and flexible down payment amount (although I feel I would want to put down 20% to remove PMI)Once Dad sells his home (easier to do than finding a duplex) he will give me about $55-65k of the profits, be the owner occupier in a duplex, go halfsies on repair/cap ex, but only wants to pay about $500 per month (he'll adjust for inflation!) 

You'll know if the tenants are in trouble, and it's easier on turnover to keep services on for repairs, etc.