The main block I have with multi family (which is the route I had intentionally intended on going ) is that because I already own a single family, I would need to come up with a substantial down payment and multi families around my area are 800k +.

Try looking into zillow/Redfin and see what your potential rents you can get near the neighborhood by filtering the bedrooms/bathrooms of the intentional property that you are planning to buy.

As of right now I know I need to add an attorney and contractor to my team to move forward.I have intentions of using a private lender and am looking for advice/guidance from anyone that has done a flip by doing so.

We purchased the home over 3 years ago with the intention of starting a family, but my partner changed her mind.  

For any property that looks interesting, I am sending the broker an email and if I don't get a response, sending an LOI and proof of funds to qualify my intent to purchase.

Unfortunately I dont have much advise but it was always My understanding the primary intentional of Landlord insurance is the access to their lawyers rather than the amount of money they cover.

STR is in less demand across the board, you should not look for property with the intention of making it a STR.

What this means is that it cannot be a fix n flip where your intent is primarily to resell.

Mom's sale - Because of #1 this makes it tough to use intent as a reason to do a 1031 even though there has been a short holding period. 

Would your intent be to purchase this property and live there for a year then rent it out to purchase another primary residence?