It’s not the most simple task unfortunately - definitely requires some technical skill.

Jake may also shy away from the effort and vulnerability required to build a healthy relationship.

Additionally, we have developed templates for tracking key metrics that we require our PMs to fill out weekly. 

There are also 'mezz' lenders (typically for larger transactions) who will cover up to 90% CLTV and require you to bring the remaining equity to the deal, and additionally there is Gap Funding in the form of unsecured personal debt.The latter can potentially be the most expensive option, but allows for true 100% financing as there are no restrictions for how to use these funds, as they are unsecured, and generally obtained through personal credit, income etc (since there is no collateral for obtaining these funds).

While they generated some cash flow, I found the effort required to manage them wasn’t worth the return.

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 ?

If you're eligible, a VA loan is your best choice since it requires $0 down, no PMI, and allows multi-family properties.

Also, as long as the house appraises, taking broker commission and using it against down payment and closing costs means lower cash requirements for me which increases my CoC returns.

I am sorry that the storm that passed through just prior to your stay required emergency roof repairs. 

Making money in real estate requires experience and starting with no or little money makes you study harder.As much as most of us probably wished for it, getting started with a lot of money in your pocket is a recipe for disaster: the temptation is to make the deal work by throwing money at it.If you want to go into real estate go with a syndicator with a good track record.