Seller is willing to take my offer and present to bank for a potential short sale.

You'll find about 70% of that, but not always from the financial / legal professionals who should be presenting it.

My family has had rental properties in the past, and I'm certain if I present my numbers with confidence and reassure the returns, I may be able to get a head start capital wise.

My family has had rental properties in the past, and I'm certain if I present my numbers with confidence and reassure the returns, I may be able to get a head start capital wise.

SF will provide with a good life but MF has the ability to create life changing wealth.MF is hard in it's own right as a syndicator but if you are looking to invest passively then the extent of your work is really about finding a syndicator you like and trust and then invest with them as soon as you like one of the deals they present you with.  

On top of the units that I own, my family has over 100 rental units in Central MA and all are self-managed, but we also have a construction company and de-leading company under the umbrella, so it's been a vertically integrated sort of deal since I was young.

Then present her with the idea of getting a coin operated machine. 

Also I'm assuming you are missing out on rent during this time because now you will have to present a new applicant and wait another 30 days. 

Once we see that you can analyze a deal and present it intelligently, we will be quite willing to get to know you enough to perhaps put the deal together.Your experience, to us, is not as important as whether you know how to find and analyze a deal and present it the way your prospective lenders expect.

Just stay consistent with your marketing techniques, be aggressive when opportunity presents itself and make offers.