Make it so that everyone wins.

My business has been in business for 30 years with excellent financials.

Because of this, many investors see this strategy as a win in 2 ways:  first, they are able to invest 100% of their gains into another investment vehicle without paying tax and therefore gain the benefit of 100% of their capital's exposure to the new investment; and second, they are essentially creating tax arbitrage between their tax bracket rate and the flat recapture rate. 

But no way can you rent it back to relatives in a win win deal.  

You're not going to win any case by showing a PA DMJ pictures of clearly damaged doors and windows and insisting that you won't fix them as long as the tenants are smoking inside.

@Michael Dumler all excellent and valid questions.

Tough to win that battle.Just my thoughts.....hopefully you prove me wrong and make all kinds of cash on the PM business and are able to create automation and outsourcing to handle all the work at minimal expense with lots of profit.

-Purchase price is $475k-expected gross rents 4440/month if all are LTR, more for STR-Current rents per month: 1 is $850, 2 are STR, one owner occupied-Fair market rents per month: $1020-1200 as LTR-We have an existing relationship with an excellent professional property manager-We have excellent credit and high salaried  W2 income (attorney)Thankful for any advice you can offer!

@Bronson SimmonsGenerally you should look for someone who sells at least 10 properties annually in the area that you are looking to buy.Someone local doing that much business or more will be able to explain what it takes to win offers in that area. 

If you're looking for property with an investment mindset you'll be able to find a good deal that will produce income and gain equity and for a house hack property, that's a WIN!