Why will likely determine how because if you are looking for cashflow vs. appreciation vs. quick capitalHow could it be househacking, brrrr, flip, long term -> You mentioned BRRRR, which is an awesome strategy but will only work in specific sectors of Chicagoland. finding the perfect brrrr in the current environment is extremely tough!

Material participation.

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.

You don't want the customer to buy materials because they buy cheap materials or wrong materials.

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

Do you mean the piece of material (either steel or concrete) used for repair, or one spot of a house that needs to be lifted?

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.

There are probably many posts that contain similar information to this one, but I thought it would be of value to future and existing investors who are starting their journey.We recently completed rehabbing a duplex we bought for $93k and rehabbed for $75k (in retrospect, we could've negotiated a lower price 🤷‍♂️ - discussion for a different post), hitting an ARV of $190k when our target ARV was $170k.Two things that stood out for me that helped us secure a higher ARV that anyone can use in their next BRRRR were:1) Fix the property to be in the top 75th percentile -> To improve our success rate, we consulted with both our agent and our PMC on what kind of materials and finishes the best properties (highest ARV Comps and Rent Rates) had in the area.

@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.