Having multiple exit strategies is always smart. 

Talk is cheap - look at his credentials before investing in a mentor.Be smart about what you do and who you work with - you can look at listed real estate but your best deal is going to come from dealing directly with sellers.Also remember creative financing techniques - nothing down deals - Control and Roll System - Delayed Settlements - Hybrid offers - and don't forget owner assisted financing and make sure you always ask for a principal mortgage.Have fun - make full disclosures and make sure you understand the laws related to mortgage foreclosures - fail to do this and you may have a paid vacation to the Gray Bar Motel (a nice little room with one small window and the food is free, but the space is restricted).Remember your goal should be CASH FLOW or EQUITY - forget the emotional appeal - it is all about numbers - understand them and you'll do well in Charm City.Charles Parrish

There are some extremely smart investors I have worked with that successfully pulled off that strategy and are set up to make sizable gains through improvements.

House hacking and moving every two years is smart financially, but could be hard on children.  

It may be a smart move to separate the jobs, keep the bank on deck for what they are good at and use commercial lending institutions that focus only on CRE loans.  

There are so many levels to fund and inefficiencies that errors and delays are likely to be amplified.A smart seller usually requires the buyer to at least be pre-screened through their lender as a condition to enter into a purchase and sale contract.

Sure there are always going to be a few people who can, but the fact is 99.9999% of people, no matter how smart you think you are can not see that peak, and can not predict what would happen after a peak.But in terms of flipping, as long as it isnt a black swan even where prices are declining 50% in a year or two, which by the way is likely only a once in a lifetime event, then you can still flip in a slowly declining market.  

Trying to be smart about this.Thanks in advance!

Then do your research and find a smart investment for the rest.  

Some of our tenants don't have computers or smart phones.