From this list I’d definitely do the due diligence in asking the tough questions and making sure it’s a win-win. 

That’s a tough spot.

Fund it with a hard money loan (Dad's down payment money) and my income as a social worker for the state.

Found property owners in tough situations to turn a deal into a win-win-win scenario.

RE investing is a long-term thing and it takes time to build up your knowledge and get that big ball moving, but once you do, it's tough to stop it! 

We decided against setting up an LLC since it’s tough to get financing with a newly formed LLC.

Finding deals in this market is really tough...but if you can find a "good deal" you won't have ANY issues finding an investor to do the deal. 

Luxury Yacht (with decent expendable income) who owns a 3 year old SFH he rents out at market rate in a class B area to stable renters may make a different decision on what to do with monthly cash inflow than Just starting out on a shoestring and a prayer blue coller worker who owns a 70 year old class C that is overdue for a rehab.That is based on personal ability to meet costs when they come due and the probability that costs will come due.That being said, it's always intelligent to budget for CAPEX using real life numbers vs IRS or guesstimate numbers.You also need money for turns, which includes carrying costs when unoccupied and etc...As well as unexpected costs, such as roof damage, or early appliance failure--such as a refrigerator.Good Luck!

Most contracting companies run pretty lean and pay their subs and workers weekly.  

That's tough. 1 hand you could invest use use the return and appreciation to pay off debt.