I have been doing a lot of research, learning and listening to learn about real estate investing in the past few years and it seems to me that your first property can really influence how quickly or slowly you could scale your business.

Will depend on several factors like the type of property, type of tenants, your risk tolerance, other assets you own, your estate planning, laws where the property is located, etc.Any lawsuits would be limited to the assets of the LLC and not your personal assets (assuming you run the LLC appropriately and the corporate veil is not pierced).

I just find the rent I need to charge to cover my "must pays" by a factor of 1.35 or greater.

I understand looking for advice on how to talk to someone or if a deal is possible given certain factors, but contracts are the core of how to execute a wholesale deal. 

Whereas the first option I’ll most likely spend the entire 40k, I’m factoring down payment, closing costs, and renovations.Let me know what ya’ll think!

Price will also be a factor in getting the most activity during this time.  

I looked at building my own but it's not just the cost but the upkeep and the hassle factor involved with it.

imo school district one of largest factors in my market. 

Keep in mind that given the current state of things lenders, title companies, and others may play a factor on time to close. 

I am not sure how much influence you will have over the process.