But also, I don't know what to look for, so who am I to know what's going to cost a lot to fix or not?

The only major issue I see is that he has had many major expenses last year due to a plumbing issue from the cast iron pipes that caused one unit to be down for a very long time and did cost a lot of money to fix.

But, yeah, you should probably keep talking to contractors.A structural engineer will be able to tell you all these things, but they cost a lot of money.

.~ The flips always cost more $ and time than I thought, which cut into my profit tremendously~ I didn't manage contractors very well (A lot of $ was wasted and stolen)~ Inspection responses cost a lot of $ ~ FHA has the 90 Day rule (an FHA Buyer can't get a loan until you own the home for 90 Days, again this was more time into the project and more $)~ I only wanted to go to these properties like 3 times during the whole rehab process, but I found myself going there about a dozen times per project.

Just like a spec builder who buys a lot, builds a home then tries to sell it for more than it cost, a spec remodeler does the same thing with an existing house.

My dad bought and sold primarily the stock of tne Fortune 500 company he worked for...back in the days when a stock trade cost a considerable chunk of change.  

We have a beautiful (and really quite ridiculous) house, two nice older cars, we eat out occasionally, just took a vacation to Costa Rica, etc.

I didn't realize it cost a bit to get it advertised on there.

Then, when you do your books, or get audited it is much easier for your accountant and auditor to do the books and audits because they won't have to ponder over and sift through your personal accounting.It may cost a little more to have personal and business accounting and taxes, but one the most-critical reasons by businesses have been successful is because we have super simple and super accurate bookkeeping systems.

I read that one person had a $1M policy, but not sure how much that would cost.Yes, umbrella policies are highly recommended as they only cost a few hundred dollars per year on average.