If your a cash basis taxpayer you can’t take the loss until realized.  

Purchase price: $275,000 Cash invested: $294,000 Sale price: $355,000 Seller was behind on pay HOA payments and in risk for losing the property.

I would recommend fixing it and then determining whether or not to sell based on cash flow and profit after the sale.

Purchase price: $15,000 Cash invested: $25,000 Sub to deal - paid the seller and wholesaler $15,000 + $7500 closing costs to assume $84,000 mortgage with a monthly PITI of $575.

Registration fees $800+ SOI $50 fees California and legal stuff-keeping it simple-easier to refinance a SFR if decide to just BRR and cash out refi in my personal name versus trying to get loan in LLC name. 

Does it cash flow?

I guess my only other option is to add padlocks onto the cash boxes on top of the regular keyed entry.

There are some people that get lucky and earn cash quickly, but they generally hide the fact that it was pure luck or how much work was involved.

But truly wholesaling is a hard business and takes a lot of up front cash to get going before you get deal flow. 

Really expedites the time it takes to reach FI when you can completely eliminate your housing payment and get into multis for such little down and start building equity/cash flow with each one.