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

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

So, we are required to file Form D with the SEC only once - for the "parent" LLC.  

Go to local Home Depot, 6am on Saturday, and look for hadnymen.Try to find one that at least has liability insurance.Also, not sure if Illinois requires handymen to be licensed, but if so, find ones that are.

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 ?

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

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.

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.

What documents do they require, what credit scores do they allow, how do they verify previous rental history, etc.?

Hi Lina, It’s exciting to hear that you’re looking to invest in a mid-term rental (MTR), and I’d love to help you navigate the financing side of things.Understanding loan options, down payment requirements, interest rates, and how lenders view MTR properties is crucial to setting yourself up for success.