It depends on your financial strength, the quality of the property, how many properties you own, etc.I like to start with one significant expense and three months of vacancy.

It sounds like you are off to a great start already especially by educating yourself! 

Hello @Camille Romero congrats on getting started on your real estate journey. 

I started listing the homes one by one as they became vacant, and we were doing okay with getting them sold - in 2012, that was no small task.Jeff called me one day and asked me for CMAs on the next few properties that would be coming up.

I am considering getting into this space (looking at some courses), but worried that its too late, and that deep local market knowledge/understanding of buyers/connection with developers etc is required to make this work, which only incumbent/long term investors will have and would be hard for a new entrant starting from scratch to catch-up...is my hypothesis valid in your opinion ?

Great start on investing!

Although the property is worth way more than the loan we are needing and the secured collateral lien is really a sure safe bet and some easy money for someone willing to take the chance that isn't in it for anything other than to flip their money for profit/wanting to add to their portfolio, this would be an good opportunity for someone just starting out in real estate investment even.

As we continued to scale, we eventually added a positions to start taking some of my wife's responsibilities. 

That was after vetting many properties eliminating them before starting out.The more you do. 

She has some stock (maybe 50k), some retirement IRA of around 100k which I believe she has started to take and then maybe 20k in her savings account.