It is most important that you have a clear understanding of the type property and the strategy you want to use (FLIP, LONG TERM BUY AND HOLD, STR, MTR).  

Once you have a consistent amount of income from your business for 2 years where you can afford to buy a primary, then I would look into house hacking.

Lastly this is my first post here so apologies in advance if I posted this wrong or in the wrong place  House hacking is perhaps the best strategy to get started in real estate.

A duplex strategy is a low-risk entry, saving on living expenses.

I love section 8 but it comes with positives and negatives just like any other strategy.

Look at their marketing strategy.

You need to identify which strategy you like best before jumping in and get extremely familiar with the process of underwriting deals.

Yes. the original lender probably will not but a new lender may- there first question is gonna be what is your exit strategy so be prepared to answer that question.

If your parents do not have experience and you are eager to learn, you should come up with a strategy with your parents so that you can start managing the existing portfolio and finding a way to grow it.First and foremost I would maximize the property as much as possible now.How well is it maintained - any deferred maintenance? 

I believe Pricelabs is offering a pricing strategy and market analysis info more in line with hotels, and that might be a good tool for you to look at.