A "rich" investor is not likely to have wasted the $100k they borrowed against their 100 yo investment property, and they likely won't be concerned at all about the vagaries of the economic cycle which could technically place them "underwater" for that property, because, they will have a large portfolio of diversified properties, and will only be leveraged at around 75% of their current book value, which means that the economy would need to to take a really steep dive for their $135k property to become only worth $50k.

If you have an inspection or walk the property with a contractor or seasoned investor they can guide you in terms of what to expect for maintenance and capex. 

In the education section there are many great book suggestions that are specifically tailored to flipping so check those out.  

If I was coaching my younger self, this is what I would recommend: Read Brandon Turner's book on Rental Property Investing https://www.amazon.com/Book-Rental-Property-Investing-Passive-ebook/dp/B018UTI2DOListening to the BP Real Estate podcast https://www.biggerpockets.com/podcastListening to the BP money podcast https://www.biggerpockets.com/moneyshowAttend your local REIA meetings to networkStart analyzing deals to get practiceEngage more on the BP forumsAll the best!

I am currently doing a BRRRR (Buy, Rehab, Rent, Refinance, Repeat) on a mutifamily Property and got the idea from Brandon Turner’s Book, “The Book on Rental Property Investing.” https://www.biggerpockets.com/rentalbook.Like I said, I’m doing buy and hold on mutifamily properties and this book is what made this possible.

Toughen up or get out of the business--or suffer the emotional roller coaster an experienced tenant can put you through.Story from my upcoming book "Excuses Tenants Provide":  "I had to use the rent money to fix my car". 

Sounds like a win in my book.

Start here:  The Ultimate Beginner’s Guide to Real Estate Wholesalinghttps://www.biggerpockets.com/renewsblog/2015/01/3...Driving for Dollars Bible: Finding Distressed Properties and Marketinghttps://www.biggerpockets.com/renewsblog/2013/05/0...

I been reading some books and listening to podcasts on how to use other people's money for downs etc.

Thanks Swanny,Looked for the book on Audible, BP Store and my library.