Should I use it to build the big house and house hack (probably around 500k) ; or should I just take out enough for a down payment on a new property.

Quote from @Nir Berko: Hey everyone,Just got my hands on a place I'm planning to fix up and rent out to a Section 8 tenant.I'm new to making a place Section 8 ready and could use some pointers.

Or hang out at places where people with money go, i.e. nice hotel bars, nice restaurants, country clubs, etc.

Quote from @Jarred Adams: Let them figure it out. 

I recommend you rent it long-term for a year while you figure out where you are trying to go.

I have a few investors buying in the local Tampa Bay area for around 400k that are renting properties out for around $4200-4400 per month based on long term rents. 

If you use property management software like TenantCloud, you can enter your listing once and it will push it out to many websites simultaneously.

There are a few options out there, but not many. 

I would think that at the closing table, the owner would have to clear the IRS lien with the sale of the property and then come out of pocket. 

In your case, since your parents own the properties and you’re helping them out, you may not be able to claim those deductions unless they pay you for your services.