Tough spot to be in.First, it sounds like your parents really want what they think is best for you; that's great! 

The quick good/bad of Section 8:- S8 tenants tend to be rougher on the property (but not always)- Paperwork/inspections/etc. can be burdensome and tough to navigate (especially initially)- People often think FMR rates are guarantee rental rates but that's not the case- Usually the rent isn't 100% subsidized and a lot of people don't realize this- S8 tenants tend to stay a lot longer than cash tenants- Obviously, the guaranteed rent portionOverall, I'm neutral on the program.

They said the reality is that generating leads is tough and I should give it a full month before evaluating the results.

Your partner may be able to trick TurboTax into "allowing" a loss by manipulating some checkboxes, but it will be against the tax rules.You have a tough dilemma.

BRRRR is tough right now.  

@Errol Graham you're in a tough position - too small for better software systems, but getting too big for spreadsheets.Stessa may be a decent option, as you should be able to track your accounting so you don't miss something or double enter a bill.Depending on the cost of QuickBooks, you may want to look into Buildium.

Thats a low LTV but without knowing or seeing the PFS, Returns and previous P&L its tough but if strong 65% even higher should be workable.  

We self manage all of our properties...really not tough. 

Flipping it tough right now unless you can buy the property direct from the Seller and (hate to say it) lowball them.

I totally understand the challenges with deal flow, especially in a tough market.